Benzofuran-7-yl uracil derivatives and herbicides

ABSTRACT

A benzofuran-7-yl uracil derivative represented by the general formula (1): ##STR1## (wherein each of X and Y is a hydrogen atom, a halogen atom or the like, R 1  is a hydrogen atom, an alkyl group or the like, R 2  is a haloalkyl group or the like, R 3  is a hydrogen atom, a halogen atom or the like, each of R 4  and R 5  which are independent of each other, is a hydrogen atom, an alkyl group, a haloalkyl group, a halogen atom, a cyano group, a phenyl group, a benzyl group, a nitro group or the like), and a herbicide containing it as an active ingredient. 
     The compound of the present invention represented by the general formula (1) exhibits excellent herbicidal effects against various weeds which cause trouble in upland fields, such as, broad leaved weeds, gramineous weeds and perennial or annual cyperaceous weeds, over a wide range from the pre-emergence to the growing stage. It can further control annual weeds and perennial weeds growing in paddy fields.

This is a 371 0f PCT/JP97/00320, filed Feb. 7,1997.

TECHNICAL FIELD

The present invention relates to novel benzofuran-7-yl uracil derivatives and herbicides containing them as active ingredients.

BACKGROUND ART

The specification of JP-A-5-262765 and the specification of JP-A-5-25165 disclose some benzofuran derivatives, the specification of JP-A-63-156787 discloses some benzopyran derivatives and benzofuran derivatives, and the specification of European Patent 626962 discloses benzothiophene derivatives and benzofuran derivatives, as they are useful as active ingredients for herbicides.

Herbicides to be used for useful crop plants, are desired to be agents which can be applied to soil or foliage and provide adequate herbicidal effects at low doses and which exhibit selectivity between crop plants and weeds. However, the herbicidal effects and the selectivity between crop plants and weeds, are influenced by the nature of soil, and phytotoxicity may sometimes be brought about to crop plants after the application, irrespective of soil treatment. From such a viewpoint, the compound disclosed in the above literatures can not necessarily be said to be satisfactory.

Under these circumstances, the present inventors have studied the herbicidal effects and the selectivity between crop plants and weeds and as a result, have found that novel benzofuran-7-yl uracil derivatives have excellent herbicidal effects and selectivity between crop plants and weeds, and have accomplished the present invention.

DISCLOSURE OF THE INVENTION

Namely, the present invention provides a benzofuran-7-yl uracil derivative represented by the general formula (1): ##STR2## [wherein X is a hydrogen atom or a halogen atom, Y is a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a haloalkyl group, an alkoxy group or a haloalkoxy group, R¹ is a hydrogen atom, an alkyl group, an amino group or a haloalkyl group, R² is an alkyl group or a haloalkyl group, R³ is a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group, each of R⁴ and R⁵ which are the same or different, is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonylalkoxy group, an alkylthio group, a haloalkylthio group, an alkenylthio group, an alkynylthio group, an alkoxycarbonylalkylthio group, an alkylsulfonyl group, a haloalkylsulfonyl group, a phenylsulfonyl group which may be substituted, a halogen atom, a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group, an alkoxyiminoalkyl group, an alkoxyiminohaloalkyl group, an alkyliminoalkyl group, a phenyliminoalkyl group which may be substituted, a hydrazonoalkyl group, an alkylhydrazonoalkyl group, a phenylhydrazonoalkyl group which may be substituted, a cyano group, a carbamoyl group (having the same or different hydrogen atoms, alkyl groups, acyl groups, haloalkylcarbonyl groups, alkylsulfonyl groups, haloalkylsulfonyl groups or phenyl groups which may be substituted, substituted on the nitrogen atom), a phenyl group which may be substituted, a benzyl group which may be substituted, a cyanoalkyl group, a carbamoylalkyl group, a thiocyanoalkyl group, a nitro group, a hydroxyamino group, an oxiranyl group which may be substituted by an alkyl group, an amino group (having the same or different hydrogen atoms, alkyl groups, haloalkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, alkylsulfonyl groups, haloalkylsulfonyl groups, phenylsulfonyl groups which may be substituted, acyl groups, haloalkylcarbonyl groups or benzoyl groups which may be substituted, substituted on the nitrogen atom), or a group represented by the general formula: ##STR3## (wherein Z is an oxygen atom or a sulfur atom, W is a group of --SO-- or a group of --SO₂ --, R⁶ is a hydrogen atom or an alkyl group, R⁷ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group or an alkylthioalkyl group, or R⁶ and R⁷ bond to each other to form a 3- to 8-membered (carbon) ring together with the carbon atom to which they are bonded, R⁸ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, a dialkylcarbamoylalkyl group, an acyl group, an alkylsulfonyl group, a haloalkylsulfonyl group, a haloalkylcarbonyl group, a monoalkylcarbamoyl group, a monoalkylthiocarbamoyl group, a dialkylcarbamoyl group, a dialkylthiocarbamoyl group or a benzoyl group which may be substituted, R⁹ is a hydrogen atom, an alkyl group, a cycloalkyl group, a haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group or a dialkylcarbamoylalkyl group, R¹⁰ is a hydrogen atom, an alkyl group, an acyl group, an alkylsulfonyl group, a haloalkylsulfonyl group or a haloalkylcarbonyl group, R¹¹ is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, an alkoxyalkyl group, an alkylthioalkyl group, a phenyl group which may be substituted, an alkoxy group, a haloalkoxy group, a benzyloxy group which may be substituted, a phenoxy group which may be substituted, or a hydroxyl group)], and a herbicide containing it as an active ingredient.

In this specification, alkyl in an alkyl group, an alkylthio group, an alkoxyalkyl group, an alkylthioalkyl group, an alkoxycarbonylalkylthio group, an alkyliminoalkyl group, a cyanoalkyl group, a carbamoylalkyl group, a thiocyanoalkyl group, an oxiranyl group which may be substituted by an alkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, a dialkylcarbamoylalkyl group, a hydroxyiminoalkyl group, an alkoxyiminoalkyl group, a phenyliminoalkyl group which may be substituted, a hydrazonoalkyl group, an alkylhydrazonoalkyl group, a phenylhydrazonoalkyl group which may be substituted and an alkylsulfonyl group, represents a C₁₋₆ straight chain or branched chain alkyl group, and, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a n-hexyl group, an isohexyl group or a 3,3-dimethylbutyl group, may be mentioned.

Haloalkyl in a haloalkyl group, a haloalkylsulfonyl group, a haloalkylcarbonyl group, a hydroxyiminohaloalkyl group and an alkoxyiminohaloalkyl group, represents a C₁₋₄ straight chain or branched chain alkyl group substituted by halogen atom(s), and, for example, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group or a pentafluoroethyl group, may be mentioned.

The halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

Alkoxy in an alkoxy group, an alkoxyalkyl group, an alkoxycarbonylalkoxy group, an alkoxycarbonylalkylthio group, an alkoxyiminoalkyl group, an alkoxyiminohaloalkyl group and an alkoxycarbonylalkyl group, represents a C₁₋₆ straight chain or branched chain alkoxy group, and, for example, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a n-pentyloxy group, an isopentyloxy group, a neopentyloxy group, a n-hexyloxy group, an isohexyloxy group or a 3,3-dimethylbutoxy group, may be mentioned.

The haloalkoxy group represents a C₁₋₄ straight chain or branched chain alkoxy group which is substituted by halogen atom(s), and, for example, a chloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a pentafluoroethoxy group, may be mentioned.

The acyl group represents a C₁₋₆ straight chain or branched chain aliphatic acyl group, and, for example, a formyl group, an acetyl group, a propionyl group, a butyryl group or a pivaloyl group, may be mentioned.

Alkenyl in an alkenyl group, an alkenyloxy group and an alkenylthio group, represents a C₂₋₆ straight chain or branched chain alkenyl group, and, for example, a vinyl group, a propenyl group, an isopropenyl group, a butenyl group, a pentenyl group or a hexenyl group, may be mentioned.

Alkynyl in an alkynyl group, an alkynyloxy group and an alkynylthio group, represents a C₂₋₆ straight chain or branched chain alkynyl group, and, for example, an ethynyl group, a propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a 3,3-dimethyl-1-butynyl group, a 4-methyl-1-pentynyl group or a 3-methyl-1-pentynyl group, may be mentioned.

The cycloalkyl group represents a C₃₋₈ cycloalkyl group, and, for example, a cyclopropyl group or a cyclohexyl group, may be mentioned.

The phenyl ring in a phenylsulfonyl group which may be substituted, a phenyliminoalkyl group which may be substituted, a phenylhydrazonoalkyl group which may be substituted, a phenoxy group which may be substituted, a benzyloxy group which may be substituted, a benzoyl group which may be substituted, a phenyl group which may be substituted, and a benzyl group which may be substituted, includes one substituted by a substituent such as a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, a nitro group or a cyano group.

Now, specific examples of the compounds of the present invention will be disclosed in Tables 1 to 24. However, the compounds of the present invention are not limited to such compounds. Further, the Compound Nos. will be referred to in the subsequent description.

                                      TABLE 1                                      __________________________________________________________________________      ##STR4##                                                                      Comp.                         m.p. (° C.)                               Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                           R.sup.4    R.sup.5                                                                          RI* n.sub.D.sup.20                               __________________________________________________________________________      1  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  H          H 127-128                                           2  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.3   H 196-197                                           3  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  C.sub.2 H.sub.5                                                                           H 142-143                                           4  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  C.sub.3 H.sub.7                                                                           H 88-89                                             5  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  C.sub.3 H.sub.7 -i                                                                        H                                                   6  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  C.sub.4 H.sub.9                                                                           H 1.5375                                            7  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  C.sub.4 H.sub.9 -i                                                                        H 1.5358                                            8  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 Br                                                                               H 168-172                                           9  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CHBr.sub.2 H 126-128                                          10  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CBr.sub.3  H Unmeasurable                                     11  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CHF.sub.2  H                                                  12  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 OH                                                                               H 198-199                                          13  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH(CH.sub.3)OH                                                                            H 154-157                                          14  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 OCH.sub.3                                                                        H 1.5389                                           15  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 OC.sub.2 H.sub.5                                                                 H 1.5379                                           16  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 OCOCH.sub.3                                                                      H 1.5347                                           17  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 OCOC.sub.2 H.sub.5                                                               H                                                  18  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH(CH.sub.3)OCOCH.sub.3                                                                   H                                                  19  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                  ##STR5##  H 160-162                                          20  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 SCH.sub.3                                                                        H Unmeasurable                                     21  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 SO.sub.2 CH.sub.3                                                                H 209-211                                          22  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 SC.sub.2 H.sub.5                                                                 H 1.5629                                           23  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 SO.sub.2 C.sub.2 H.sub.5                                                         H 212-215                                          24  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 N(CH.sub.3).sub.2                                                                H                                                  25  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                                         H 1.5331                                           26  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  Cl         H 180-182                                          27  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H  Br         H                                                  __________________________________________________________________________      *RI: Refractive index                                                    

                                      TABLE 2                                      __________________________________________________________________________     Comp.                           m.p. (° C.)                             Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4       R.sup.5                                                                          RI* n.sub.D.sup.20                             __________________________________________________________________________     28  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3    H 193-194                                        29  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                            H Unmeasurable                                   30  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7                                                                            H Unmeasurable                                   31  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7 -i                                                                         H 128-129                                        32  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR6##     H                                                33  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHO           H 180-183                                        34  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═NOH    H                                                35  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═NOCH.sub.3                                                                            H Unmeasurable                                   36  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOH                                                                          H 263-266                                        37  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOCH.sub.3                                                                   H 176-178                                        38  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOC.sub.2 H.sub.5                                                            H                                                39  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NCH.sub.3                                                                    H                                                40  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NNHCH.sub.3                                                                  H                                                41  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CN            H                                                42  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOH          H 267-268                                                                        (decomposed)                                   43  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOCH.sub.3   H 194-196                                        44  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.2 H.sub.5                                                                           H 1.5453                                         45  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.3 H.sub.7 -i                                                                        H Unmeasurable                                   46  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.5 H.sub.11                                                                          H                                                47  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR7##     H                                                48  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR8##     H                                                49  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONH.sub.2    H                                                50  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONHCH.sub.3  H                                                51  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CON(CH.sub.3).sub.2                                                                          H                                                52  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONHC.sub.2 H.sub.5                                                                          H                                                53  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR9##     H                                                54  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR10##    H                                                55  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR11##    H                                                56  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR12##    H                                                57  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR13##    H                                                58  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR14##    H                                                59  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NO.sub.2      H                                                __________________________________________________________________________

                                      TABLE 3                                      __________________________________________________________________________     Comp.                             m.p. (° C.)                           Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4   R.sup.5 RI n.sub.D.sup.20                            __________________________________________________________________________     60  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NH.sub.2  H                                                    61  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCH.sub.3                                                                             H                                                    62  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCH.sub.2 Cl                                                                          H                                                    63  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCF.sub.3                                                                             H                                                    64  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR15##                                                                               H                                                    65  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CH.sub.3                                                                      H                                                    66  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CF.sub.3                                                                      H                                                    67  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CH.sub.2 Cl                                                                   H                                                    68  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CHF.sub.2                                                                     H                                                    69  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR16##                                                                               H                                                    70  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.3                                                                               181-183                                      71  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  C.sub.2 H.sub.5                                                                        130-131                                      72  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  C.sub.3 H.sub.7                                                                        1.5287                                       73  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  C.sub.3 H.sub.7 -i                                   74  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  C.sub.4 H.sub.9                                                                        1.5398                                       75  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                  ##STR17##                                                                             195-197                                      76  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  SCH.sub.3                                            77  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  Br                                                   78  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  Cl      157-160                                      79  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 OH                                                                             97-100                                      80  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 OCOCH.sub.3                                                                   168-170                                      81  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 OCH.sub.3                                   82  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 OC.sub.2 H.sub.5                            83  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 SCH.sub.3                                                                     157-158                                      84  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 SO.sub.2 CH.sub.3                                                             209-211                                      85  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH.sub.2 N(CH.sub.3).sub.2                           86  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  COOH    217-220                                      87  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  COOCH.sub.3                                                                            1.5440                                       88  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  COOC.sub.2 H.sub.5                                                                     1.5489                                       89  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  COOC.sub.3 H.sub.7 -i                                                                  154-156                                      90  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  COOC.sub.5 H.sub.11                                                                    1.5299                                       91  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CHO     148-150                                      92  F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3  CH═NOH                                                                             82-84                                        __________________________________________________________________________

                                      TABLE 4                                      __________________________________________________________________________     Comp.                            m.p. (° C.)                            Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                           R.sup.5       RI n.sub.D.sup.20                             __________________________________________________________________________      93 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CH═NOCH.sub.3                                                                            1.5483                                         94 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CN                                                           95 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CONH.sub.2    102-105                                        96 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CONHCH.sub.3                                                 97 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CONHC.sub.2 H.sub.5                                          98 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CON(CH.sub.3).sub.2                                                                          90-93                                          99 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR18##                                                  100 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR19##                                                  101 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COCH.sub.3    138-140                                       102 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COC.sub.2 H.sub.5                                                                            1.5496                                        103 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COCH.sub.2 Cl 77-80                                         104 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COCF.sub.3                                                  105 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CH.sub.3                                           106 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CF.sub.3                                           107 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CH.sub.2 Cl                                        108 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CHF.sub.2                                          109 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CH(CH.sub.3)OH                                              110 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOH                                                                          108-111                                       111 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOCH.sub.3                                                                   65-67                                         112 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOC.sub.2 H.sub.5                           113 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NCH.sub.3                                   114 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NNHCH.sub.3                                                                  187-190                                       115 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR20##                                                  116 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR21##    117-120                                       117 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR22##    192-194                                       118 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR23##                                                  119 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NO.sub.2      Unmeasurable                                  120 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NH.sub.2                                                    121 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                         122 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CF.sub.3                                         123 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CH.sub.2 Cl                                      124 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CHF.sub.2                                        125 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCH.sub.3  209-211                                       __________________________________________________________________________

                                      TABLE 5                                      __________________________________________________________________________     Comp.                             m.p. (° C.)                           Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                           R.sup.5        RI n.sub.D.sup.20                            __________________________________________________________________________     126 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCF.sub.3                                                127 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCH.sub.2 Cl                                             128 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR24##                                                  129 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR25##                                                  130 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR26##                                                  131 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR27##                                                  132 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR28##                                                  133 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR29##                                                  134 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR30##                                                  135 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR31##                                                  136 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.3                                                    137 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.2 OH                                                 138 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.2 OCOCH.sub.3                                        139 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.2 OCH.sub.3                                          140 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COOH           114-116                                      141 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CHO            Unmeasurable                                 142 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COOCH.sub.3    1.5341                                       143 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COOC.sub.3 H.sub.7 -i                                                                         1.5229                                       144 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH═NOCH.sub.3                                           145 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH═NNHCH.sub.3                                          146 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   Cl                                                          147 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COCH.sub.3     1.5503                                       148 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   C(CH.sub.3)═NOH                                         149 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   C(CH.sub.3)═NOCH.sub.3                                  150 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   C(CH.sub.3)═NNHCH.sub.3                                 151 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    ##STR32##                                                  152 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COC.sub.2 H.sub.5                                                                             139-140                                      153 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   COC.sub.3 H.sub.7 -i                                                                          115-117                                      154 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    ##STR33##                                                  155 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   NO.sub.2                                                    156 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   NH.sub.2                                                    157 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   NHCOCH.sub.3                                                158 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   NHSO.sub.2 CH.sub.3                                         __________________________________________________________________________

                                      TABLE 6                                      __________________________________________________________________________     Comp.                              m.p. (° C.)                          Nos.                                                                               X Y R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                            R.sup.4                                                                            R.sup.5    RI n.sub.D.sup.20                           __________________________________________________________________________     159     CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    NHSO.sub.2 CF.sub.3                                    160     CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                     ##STR34##                                             161     CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                     ##STR35##                                             162 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    CONHCH.sub.3                                           163 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    CON(CH.sub.3).sub.2                                    164 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7                                                                    CH.sub.3                                               165 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7                                                                    COCH.sub.3 1.5362                                      166 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7                                                                    COOCH.sub.3                                                                               103-104                                     167 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7                                                                    CH.sub.2 OCH.sub.3                                     168 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7 -i                                                                 CH.sub.3                                               169 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7 -i                                                                 COCH.sub.3                                             170 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7 -i                                                                 COOCH.sub.3                                            171 F Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7 -i                                                                 CH.sub.2 OCH.sub.3                                     172 F Cl                                                                               H   CF.sub.3                                                                           H   CH.sub.3                                                                           H          172-174                                     173 F Cl                                                                               C.sub.2 H.sub.5                                                                    CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                      174 F Cl                                                                               C.sub.3 H.sub.7                                                                    CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                      175 F Cl                                                                               CH.sub.2 Cl                                                                        CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                      176 F Cl                                                                               CHF.sub.2                                                                          CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                      177 F Cl                                                                               H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                      178 F Cl                                                                               H   CF.sub.3                                                                           CH.sub.2 Cl                                                                        CH.sub.3                                                                           H                                                      179 F Cl                                                                               H   CF.sub.3                                                                           Cl  CH.sub.3                                                                           H                                                      180 F Cl                                                                               H   CF.sub.3                                                                           Br  CH.sub.3                                                                           H                                                      181 F Cl                                                                               H   CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                      182 F Cl                                                                               CH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                      183 F Cl                                                                               CHF.sub.2                                                                          CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                      184 F Cl                                                                               H   CH.sub.3                                                                           Cl  CH.sub.3                                                                           H                                                      185 F Cl                                                                               H   CH.sub.2 Cl                                                                        H   CH.sub.3                                                                           H                                                      186 F Cl                                                                               CH.sub.3                                                                           CH.sub.2 Cl                                                                        H   CH.sub.3                                                                           H                                                      187 F Cl                                                                               H   CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H          154-155                                     188 F Cl                                                                               H   CF.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H                                                      189 F Cl                                                                               H   CF.sub.3                                                                           Cl  C.sub.2 H.sub.5                                                                    H                                                      190 F Cl                                                                               CH.sub.2 Cl                                                                        CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                      191 F Cl                                                                               CHF.sub.2                                                                          CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                      __________________________________________________________________________

                                      TABLE 7                                      __________________________________________________________________________     Comp.                           m.p. (° C.)                             Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4    R.sup.5                                                                             RI n.sub.D.sup.20                              __________________________________________________________________________     192 F Cl                                                                               CHF.sub.2                                                                         CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                           COOCH.sub.3                                         193 F Cl                                                                               CHF.sub.2                                                                         CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                           H                                                   194 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          Cl                                                                               C.sub.2 H.sub.5                                                                           H                                                   195 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H H          H    142-144                                        196 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3   H    206-207                                        197 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                           H    159-160                                        198 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                           H    159-161                                        199 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7 -i                                                                        H                                                   200 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9                                                                           H    101-102                                        201 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9 -i                                                                        H    129-131                                        202 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Br                                                                               H    200-202                                        203 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHBr.sub.2 H                                                   204 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CBr.sub.3  H                                                   205 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHF.sub.2  H                                                   206 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 OH                                                                               H    179-181                                        207 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                            H    85-86                                          208 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 OCH.sub.3                                                                        H    141-143                                        209 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 OC.sub.2 H.sub.5                                                                 H    93-96                                          210 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 OCOCH.sub.3                                                                      H    135-138                                        211 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 OCOC.sub.2 H.sub.5                                                               H                                                   212 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCOCH.sub.3                                                                   H                                                   213 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR36## H    180-182                                        214 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SCH.sub.3                                                                        H                                                   215 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 CH.sub.3                                                                H                                                   216 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SC.sub.2 H.sub.5                                                                 H                                                   217 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5                                                         H                                                   218 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 NHCH.sub.3                                                                       H                                                   219 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 N(C.sub.2 H.sub.5).sub.2                                                         H    1.5420                                         220 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H Cl         H                                                   221 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H Br         H                                                   222 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3 H    181-182                                        223 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                         H                                                   224 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7                                                                         H                                                   __________________________________________________________________________

                                      TABLE 8                                      __________________________________________________________________________     Comp.                           m.p. (° C.)                             Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4       R.sup.5                                                                          RI n.sub.D.sup.20                              __________________________________________________________________________     225 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7 -i                                                                         H                                                226 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR37##    H                                                227 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHO           H 233-235                                        228 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OCH.sub.3).sub.2                                                                          H 1.5416                                         229 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═NOH    H                                                230 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═NOCH.sub.3                                                                            H 179-181                                        231 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═NNHCH.sub.3                                                                           H Unmeasurable                                   232 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOH                                                                          H                                                233 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOCH.sub.3                                                                   H 172-176                                        234 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NOC.sub.2 H.sub.5                                                            H                                                235 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NCH.sub.3                                                                    H                                                236 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═NNHCH.sub.3                                                                  H                                                237 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CN            H                                                238 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOH          H 270-273                                        239 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOCH.sub.3   H 137-138                                        240 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.2 H.sub.5                                                                           H 116-117                                        241 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.3 H.sub.7 -i                                                                        H 144-145                                        242 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COOC.sub.5 H.sub.11                                                                          H                                                243 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR38##    H                                                244 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR39##    H                                                245 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONH.sub.2    H 273-275                                        246 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONHCH.sub.3  H 287-288                                        247 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CON(CH.sub.3).sub.2                                                                          H Unmeasurable                                   248 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CONHC.sub.2 H.sub.5                                                                          H 225-226                                        249 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR40##    H 289-290                                        250 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR41##    H 294-296                                        251 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR42##    H >300                                           252 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR43##    H 254-256                                        253 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR44##    H 177-180                                        254 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR45##    H                                                255 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR46##    H                                                256 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NO.sub.2      H                                                __________________________________________________________________________

                                      TABLE 9                                      __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                               R.sup.5 RI n.sub.D.sup.20                               __________________________________________________________________________     257 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NH.sub.2                                                                              H                                                       258 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCH.sub.3                                                                          H                                                       259 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCH.sub.2 Cl                                                                       H                                                       260 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHCOCF.sub.3                                                                          H                                                       261 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CH.sub.3                                                                   H                                                       262 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CF.sub.3                                                                   H                                                       263 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CH.sub.2 Cl                                                                H                                                       264 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NHSO.sub.2 CHF.sub.2                                                                  H                                                       265 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.3                                                                               152-153                                         266 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              C.sub.2 H.sub.5                                                                        141-142                                         267 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              C.sub.3 H.sub.7                                                                        1.5461                                          268 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              C.sub.3 H.sub.7 -i                                      269 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              C.sub.4 H.sub.9                                                                        1.5557                                          270 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                               ##STR47##                                                                             Unmeasurable                                    271 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              SCH.sub.3                                               272 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              Br      1.5632                                          273 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              Cl                                                      274 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 OH                                             275 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 OCOCH.sub.3                                    276 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                      277 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 OC.sub.2 H.sub.5                               278 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 SCH.sub.3                                      279 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 SO.sub.2 CH.sub.3                              280 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH.sub.2 N(CH.sub.3).sub.2                              281 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COOH                                                    282 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COOCH.sub.3                                             283 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COOC.sub.2 H.sub.5                                      284 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COOC.sub.3 H.sub.7 -i                                   285 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COOC.sub.5 H.sub.11                                     286 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CHO                                                     287 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH═NCH                                              288 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              CH═NOCH.sub.3                                       289 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                              COCH.sub.3                                                                             172-174                                         __________________________________________________________________________

                                      TABLE 10                                     __________________________________________________________________________     Comp.                            m.p. (° C.)                            Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                           R.sup.5       RI n.sub.D.sup.20                             __________________________________________________________________________     290 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COC.sub.2 H.sub.5                                           291 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COCH.sub.2 Cl                                               292 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          COCF.sub.3                                                  293 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CH.sub.3                                           294 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CF.sub.3                                           295 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CH.sub.2 Cl                                        296 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          SO.sub.2 CHF.sub.2                                          297 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          CH(CH.sub.3)OH                                              298 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOH                                                                          248-250                                       299 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOCH.sub.3                                                                   167-168                                       300 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          C(CH.sub.3)═NOC.sub.2 H.sub.5                           301 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR48##    203-205                                       302 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR49##                                                  303 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NO.sub.2      174-175                                       304 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NH.sub.2                                                    305 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHOH          134-136                                       306 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CH.sub.3                                         307 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CF.sub.3                                         308 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CH.sub.2 Cl                                      309 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHSO.sub.2 CHF.sub.2                                        310 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCH.sub.3  290-292                                       311 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCF.sub.3                                                312 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                          NHCOCH.sub.2 Cl                                             313 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR50##                                                  314 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR51##                                                  315 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR52##                                                  316 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR53##                                                  317 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR54##                                                  318 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR55##                                                  319 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR56##                                                  320 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           ##STR57##                                                  321 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.3                                                    322 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                   CH.sub.2 OH                                                 __________________________________________________________________________

                                      TABLE 11                                     __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                            R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                            R.sup.5   RI n.sub.D.sup.20                               __________________________________________________________________________     323 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CH.sub.2 OCOCH.sub.3                                      324 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CH.sub.2 OCH.sub.3                                        325 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CHO       122-124                                         326 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    COOH                                                      327 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          R C.sub.2 H.sub.5                                                                    COOCH.sub.3                                               328 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    COOC.sub.3 H.sub.7 -i                                     329 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    Cl                                                        330 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    COCH.sub.3                                                                               1.5662                                          331 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    C(CH.sub.3)═NOH                                                                      102-105                                         332 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    C(CH.sub.3)═NOCH.sub.3                                                               1.5442                                          333 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    COC.sub.2 H.sub.5                                         334 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    COC.sub.3 H.sub.7 -i                                                                     Unmeasurable                                    335 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     ##STR58##                                                336 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CH.sub.2 SCH.sub.3                                        337 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CH.sub.2 SO.sub.2 CH.sub.3                                338 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CONHCH.sub.3                                              339 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                    CON(CH.sub.3).sub.2                                       340 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     ##STR59##                                                341 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                    CH.sub.3                                                  342 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                    COCH.sub.3                                                343 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                    COOCH.sub.3                                               344 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                    CH.sub.2 OCH.sub.3                                        345 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7 -i                                                                 CH.sub.3                                                  346 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7 -i                                                                 COCH.sub.3                                                347 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7 -i                                                                 COOCH.sub.3                                               348 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.3 H.sub.7 -i                                                                 CH.sub.2 OCH.sub.3                                        349 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H C.sub.4 H.sub.9                                                                    COCH.sub.3                                                                               1.5449                                          350 H Cl                                                                               CH.sub.3                                                                           CF.sub.3                                                                          H CH.sub.2 Br                                                                        Br        188-191                                         351 H Cl                                                                               H   CF.sub.3                                                                          H CH.sub.3                                                                           H                                                         352 H Cl                                                                               C.sub.2 H.sub.5                                                                    CF.sub.3                                                                          H CH.sub.3                                                                           H                                                         353 H Cl                                                                               C.sub.3 H.sub.7                                                                    CF.sub.3                                                                          H CH.sub.3                                                                           H                                                         354 H Cl                                                                               CH.sub.2 Cl                                                                        CF.sub.3                                                                          H CH.sub.3                                                                           H                                                         355 H Cl                                                                               CHF.sub.2                                                                          CF.sub.3                                                                          H CH.sub.3                                                                           H                                                         __________________________________________________________________________

                                      TABLE 12                                     __________________________________________________________________________     Comp.                         m.p. (° C.)                               Nos.                                                                               X Y  R.sup.1                                                                            R.sup.2                                                                            R.sup.3                                                                            R.sup.4                                                                            R.sup.5                                                                             RI n.sub.D.sup.20                                __________________________________________________________________________     356 H Cl H   CF.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H                                                     357 H Cl H   CF.sub.3                                                                           CH.sub.2 Cl                                                                        CH.sub.3                                                                           H                                                     358 H Cl H   CF.sub.3                                                                           Cl  CH.sub.3                                                                           H                                                     359 H Cl H   CF.sub.3                                                                           Br  CH.sub.3                                                                           H                                                     360 H Cl H   CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                     361 H Cl CH.sub.3                                                                           CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                     362 H Cl CHF.sub.2                                                                          CH.sub.3                                                                           H   CH.sub.3                                                                           H                                                     363 H Cl H   CH.sub.3                                                                           Cl  CH.sub.3                                                                           H                                                     364 H Cl H   CH.sub.2 Cl                                                                        H   CH.sub.3                                                                           H                                                     365 H Cl CH.sub.3                                                                           CH.sub.2 Cl                                                                        H   CH.sub.3                                                                           H                                                     366 H Cl H   CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                     367 H Cl H   CF.sub.3                                                                           CH.sub.3                                                                           C.sub.2 H.sub.5                                                                    H                                                     368 H Cl H   CF.sub.3                                                                           Cl  C.sub.2 H.sub.5                                                                    H                                                     369 H Cl CH.sub.2 Cl                                                                        CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                     370 H Cl CHF.sub.2                                                                          CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                     371 H Cl CHF.sub.2                                                                          CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                           372 H Cl CHF.sub.2                                                                          CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H                                                     373 H Cl CH.sub.3                                                                           CF.sub.3                                                                           Cl  C.sub.2 H.sub.5                                                                    H                                                     374 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   H   H    151-152                                          375 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           H    176-178                                          376 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           COCH.sub.3                                                                          Unmeasurable                                     377 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           COOCH.sub.3                                           378 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           CH.sub.2 OH                                           379 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    H    156-158                                          380 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    COCH.sub.3                                            381 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    COOCH.sub.3                                           382 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.2 H.sub.5                                                                    CH.sub.2 OH                                           383 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7                                                                    H    137-140                                          384 F F  CH.sub.3                                                                           CF.sub.3                                                                           H   C.sub.3 H.sub.7 -i                                                                 H                                                     385 Cl                                                                               H  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                     386 F H  CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                     387 F CN CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                     388 F CH.sub.3                                                                          CH.sub.3                                                                           CF.sub.3                                                                           H   CH.sub.3                                                                           H                                                     __________________________________________________________________________

                                      TABLE 13                                     __________________________________________________________________________     Comp.                             m.p. (° C.)                           Nos.                                                                               X Y   R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5                                                                               RI n.sub.D.sup.20                            __________________________________________________________________________     389 F CF.sub.3                                                                           CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 H                                                   390 F OCH.sub.3                                                                          CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 H                                                   391 F OCHF.sub.2                                                                         CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 H                                                   392 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Cl                                                                             H      181-182                                      393 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)Cl                                                                          H      1.5639                                       394 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)Br                                                                          H      1.5562                                       395 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCH.sub.3                                                                   H                                                   396 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)Cl                                                                   H                                                   397 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR60##                                                                              H      85-87                                        398 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.4 H.sub.9 -n                                                                    H      95-97                                        399 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.2 Cl                                                                           H                                                   400 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.2 Br                                                                           H      105-106                                      401 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.2 H.sub.5                                                                   H      Unmeasurable                                 402 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.3 H.sub.7                                                                   H      66-67                                        403 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.3 H.sub.7 -i                                                                H                                                   404 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.tbd.CH                                                                          H      143-144                                      405 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)CH═CH.sub.2                                                                   H      87-88                                        406 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SC.sub.3 H.sub.7                                                               H      1.5656                                       407 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 C.sub.3 H.sub.7                                                       H      156-157                                      408 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SC.sub.3 H.sub.7 -i                                                            H                                                   409 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 C.sub.3 H.sub.7 -i                                                    H      125-127                                      410 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SC.sub.4 H.sub.9                                                               H      1.5512                                       411 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 C.sub.4 H.sub.9                                                       H      103-104                                      412 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH═CH.sub.2                                                                         H      108-109                                      413 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H C.tbd.H                                                      414 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 CH.sub.2 CF.sub.3                                                     H                                                   415 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR61##                                                                              H                                                   416 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCH.sub.2 CF.sub.3                                  417 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR62##                                                                            154-156                                      418 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR63##                                                                            116-117                                      419 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COC.sub.3 H.sub.7                                                                     124-126                                      420 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COC.sub.3 H.sub.7 -i                                                                  1.5344                                       421 F Cl  CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COC.sub.4 H.sub.9                                                                     104-105                                      __________________________________________________________________________

                                      TABLE 14                                     __________________________________________________________________________     Comp.                         m.p. (° C.)                               Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4                                                                             R.sup.5  RI n.sub.D.sup.20                                __________________________________________________________________________     422 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            COCH.sub.2 Br                                                                           1.5650                                           423 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            CH.sub.2 Cl                                                                             177-179                                          424 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            CH(CH.sub.3)OH                                                                          1.5345                                           425 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            C(C.sub.3 H.sub.7)═NOCH.sub.3                                                       1.5397                                           426 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            C(CH.sub.2 Cl)═NOH                                                                  107-109                                          427 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            OCH.sub.3                                                                               57-60                                            428 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            OC.sub.2 H.sub.5                                          429 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            OC.sub.3 H.sub.7                                          430 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            OC.sub.3 H.sub.7 -i                                       431 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                            CH(CH.sub.3)OCH.sub.3                                     432 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     COOC.sub.2 H.sub.5                                                                      133-135                                          433 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     COOC.sub.3 H.sub.7                                                                      124-125                                          434 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     COOC.sub.4 H.sub.9                                        435 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     COC.sub.3 H.sub.7                                                                       1.5420                                           436 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                      ##STR64##                                                                              128-129                                          437 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     CH(CH.sub.3)OH                                            438 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                     CH(CH.sub.3)OCH.sub.3                                     439 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COOH     147-148                                          440 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     CONH.sub.2                                                                              187-188                                          441 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     CONHCH.sub.3                                                                            198-200                                          442 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     CON(CH.sub.3).sub.2                                                                     1.5336                                           443 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COOC.sub.3 H.sub.7 -i                                                                   1.5290                                           444 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COC.sub.2 H.sub.5                                                                       1.5441                                           445 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COC.sub.3 H.sub.7                                                                       1.5401                                           446 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COC.sub.3 H.sub.7 -i                                                                    Unmeasurable                                     447 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COCH.sub.2 Cl                                                                           129-130                                          448 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     COCH.sub.2 Br                                                                           110-111                                          449 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     CH.sub.2 OH                                                                             1.5255                                           450 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     CHO      123-124                                          451 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     C(CH.sub.3)═NOC.sub.3 H.sub.7 -i                                                    1.5304                                           452 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                     C(CH.sub.3)═NOCH.sub.3                                                              1.5332                                           453 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                          CH.sub.3 117-118                                          454 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                   CH.sub.3 119-120                                          __________________________________________________________________________

                                      TABLE 15                                     __________________________________________________________________________     Comp.                            m.p. (° C.)                            Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5 RI n.sub.D.sup.20                             __________________________________________________________________________     455 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7                                                                       CH.sub.3                                                                               1.5498                                        456 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)CH.sub.3                                                                          CH.sub.3                                                                               130-131                                       457 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.2 H.sub.5                                                                   CH.sub.3                                                                               141-142                                       458 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.3 H.sub.7                                                                   CH.sub.3                                                                               1.5392                                        459 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              C.sub.2 H.sub.5                                                                        170-171                                       460 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                       C.sub.2 H.sub.5                                                                        Unmeasurable                                  461 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.3 H.sub.7                                                                       C.sub.2 H.sub.5                                                                        116-117                                       462 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)CH.sub.3                                                                          C.sub.2 H.sub.5                                                                        122-123                                       463 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                        Unmeasurable                                  464 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(OH)C.sub.3 H.sub.7                                                                   C.sub.2 H.sub.5                                                                        Unmeasurable                                  465 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 C(CH.sub.3)═NOCH.sub.3                                                             114-116                                       466 H Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         NHCOCH.sub.3                                                                           156-158                                       467 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.3                                                                   H       1.5394                                        468 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCH.sub.3                                                                  H       84-86                                         469 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.3                                                           H       182-183                                       470 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.2 H.sub.5                                                            H       1.5540                                        471 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.2 H.sub.5                                                           H       53-54                                         472 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5                                                    H       73-75                                         473 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.3 H.sub.7                                                            H       1.5325                                        474 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.3 H.sub.7                                                           H       1.5585                                        475 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.3 H.sub.7                                                    H       67-68                                         476 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.3 H.sub.7 -i                                                         H       1.5461                                        477 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.3 H.sub.7 -i                                                        H       1.5470                                        478 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.3 H.sub.7 -i                                                 H       159-161                                       479 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.4 H.sub.9                                                            H       1.5435                                        480 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.4 H.sub.9                                                           H       1.5472                                        481 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.4 H.sub.9                                                    H       125-126                                       482 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.3                                                            H       1.5540                                        483 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOCH.sub.3                                                           H       83-85                                         484 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3                                                    H       83-86                                         485 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SC.sub.2 H.sub.5                                                     H       1.5562                                        486 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOC.sub.2 H.sub.5                                                    H       1.5231                                        487 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 C.sub.2 H.sub.5                                             H       178-179                                       __________________________________________________________________________

                                      TABLE 16                                     __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4      R.sup.5                                                                          RI n.sub.D.sup.20                               __________________________________________________________________________     488 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SC.sub.3 H.sub.7                                                         H                                                 489 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOC.sub.3 H.sub.7                                                        H                                                 490 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 C.sub.3 H.sub.7                                                 H                                                 491 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SC.sub.3 H.sub.7 -i                                                      H                                                 492 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOC.sub.3 H.sub.7 -i                                                     H                                                 493 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 C.sub.3 H.sub.7 -i                                              H                                                 494 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SCH.sub.3                                                                H                                                 495 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SOCH.sub.3                                                               H                                                 496 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SO.sub.2 CH.sub.3                                                        H                                                 497 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SC.sub.2 H.sub.5                                                         H                                                 498 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SOC.sub.2 H.sub.5                                                        H                                                 499 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7)SO.sub.2 C.sub.2 H.sub.5                                                 H                                                 500 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SCH.sub.3                                                             H                                                 501 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SOCH.sub.3                                                            H 1.5281                                          502 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SO.sub.2 CH.sub.3                                                     H 149-150                                         503 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SC.sub.2 H.sub.5                                                      H                                                 504 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SOC.sub.2 H.sub.5                                                     H 1.5404                                          505 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.3 H.sub.7 -i)SO.sub.2 C.sub.2 H.sub.5                                              H 1.5390                                          506 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 SCH.sub.3                                                                 H                                                 507 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 SOCH.sub.3                                                                H                                                 508 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 SO.sub.2 CH.sub.3                                                         H 227-230                                         509 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(C.sub.2 H.sub.5)SOCH.sub.3                                                      H                                                 510 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3                                               H 85-87                                           511 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(C.sub.3 H.sub.7)SO.sub.2 CH.sub.3                                               H 92-93                                           512 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(CH.sub.2 OCH.sub.3)SOCH.sub.3                                                   H                                                 513 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(CH.sub.2 OCH.sub.3)SO.sub.2 CH.sub.3                                            H 1.5365                                          514 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)(CH.sub.2 SCH.sub.3)SO.sub.2 CH.sub.3                                            H                                                 515 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCF.sub.3                                                                       H Unmeasurable                                    516 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCF.sub.3                                                                      H                                                 517 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CF.sub.3                                                               H                                                 518 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCHF.sub.2                                                                      H                                                 519 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCHF.sub.2                                                                     H                                                 520 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CHF.sub.2                                                              H                                                 __________________________________________________________________________

                                      TABLE 17                                     __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4      R.sup.5                                                                          RI n.sub.D.sup.20                               __________________________________________________________________________     521 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SCH.sub.2 COOCH.sub.3                                                              H 1.5390                                          522 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SOCH.sub.2 COOCH.sub.3                                                             H                                                 523 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 CH.sub.2 COOCH.sub.3                                                      H                                                 524 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.2 COOCH.sub.3                                                           H 1.5411                                          525 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.3 H.sub.6 Cl                                                             H                                                 526 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.3 H.sub.6 Cl                                                            H                                                 527 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.2 H.sub.4 COOCH.sub.3                                                    H                                                 528 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.2 H.sub.4 COOCH.sub.3                                            H                                                 529 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.2 CONHCH.sub.3                                                          H                                                 530 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.2 CONHCH.sub.3                                                  H                                                 531 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.2 CON(CH.sub.3).sub.2                                                   H                                                 532 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.2 CON(CH.sub.3).sub.2                                           H                                                 533 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.2 COOH                                                                  H                                                 534 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCH.sub.2 COOH                                                                 H                                                 535 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.2 COOH                                                          H                                                 536 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR65##   H                                                 537 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR66##   H                                                 538 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H                                                                                 ##STR67##   H                                                 539 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SOCH.sub.3                                                                         H 127-129                                         540 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SH                                                                              H                                                 541 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCOCH.sub.3                                                                     H                                                 542 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCON(CH.sub.3).sub.2                                                            H                                                 543 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCONHCH.sub.3                                                                   H                                                 544 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCSN(CH.sub.3).sub.2                                                            H                                                 545 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCSNHCH.sub.3                                                                   H                                                 546 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)Br                                                                              H 1.5389                                          547 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCF.sub.3                                                                       H 1.5140                                          548 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCN                                                                             H 1.5450                                          549 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 OH                                                                        H 160-161                                         550 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CF.sub.3                                                               H                                                 551 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)NHSO.sub.2 CF.sub.3                                                             H Unmeasurable                                    552 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.2 Cl)SCH.sub.3                                                                    H                                                 553 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.2 Cl)SOCH.sub.3                                                                   H                                                 __________________________________________________________________________

                                      TABLE 18                                     __________________________________________________________________________     Comp.                         m.p. (° C.)                               Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                            R.sup.3                                                                          R.sup.4    R.sup.5                                                                          RI n.sub.D.sup.20                                __________________________________________________________________________     554 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 Cl)SO.sub.2 CH.sub.3                                                          H                                                  555 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH═CH.sub.2)SCH.sub.3                                                              H                                                  556 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH═CH.sub.2)SOCH.sub.3                                                             H                                                  557 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH═CH.sub.2)SO.sub.2 CH.sub.3                                                      H                                                  558 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(C.tbd.CH)SCH.sub.3                                                                     H                                                  559 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(C.tbd.CH)SOCH.sub.3                                                                    H                                                  560 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(C.tbd.CH)SO.sub.2 CH.sub.3                                                             H                                                  561 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR68## H                                                  562 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR69## H                                                  563 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR70## H                                                  564 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR71## H                                                  565 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 OCH.sub.3)SCH.sub.3                                                           H                                                  566 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 OCH.sub.3)SO.sub.2 CH.sub.3                                                   H                                                  567 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 SCH.sub.3)SCH.sub.3                                                           H                                                  568 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CF.sub.3)SCH.sub.3                                                                     H                                                  569 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CF.sub.3)SOCH.sub.3                                                                    H                                                  570 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CF.sub.3)SO.sub.2 CH.sub.3                                                             H                                                  571 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NHCH.sub.3                                                                    H Unmeasurable                                     572 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)N(CH.sub.3).sub.2                                                             H 1.5341                                           573 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NHSO.sub.2 CF.sub.3                                                           H                                                  574 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NHSO.sub.2 CH.sub.3                                                           H                                                  575 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NHCOCH.sub.3                                                                  H                                                  576 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NHCOCH.sub.2 Cl                                                               H                                                  577 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)SCN                                                                           H 60-63                                            578 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR72## H 113-115                                          579 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 Cl)OH                                                                         H                                                  580 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 Br)OH                                                                         H                                                  581 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CF.sub.3)OH                                                                            H                                                  582 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 OCH.sub.3)OH                                                                  H                                                  583 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.2 SCH.sub.3)OH                                                                  H                                                  584 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCH.sub.3                                                                     H 120-121                                          585 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OC.sub.2 H.sub.5                                                              H 1.5080                                           __________________________________________________________________________

                                      TABLE 19                                     __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                            R.sup.3                                                                          R.sup.4     R.sup.5                                                                          RI n.sub.D.sup.20                               __________________________________________________________________________     586 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OC.sub.3 H.sub.7                                                               H 1.5241                                          587 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCHF.sub.2                                                                     H                                                 588 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR73##  H                                                 589 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCH.sub.2 COOCH.sub.3                                                          H                                                 590 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCH.sub.2 CON(CH.sub.3).sub.2                                                  H                                                 591 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCOCH.sub.3                                                                    H 1.5251                                          592 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCON(CH.sub.3).sub.2                                                           H 1.5937                                          593 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCSN(CH.sub.3).sub.2                                                           H                                                 594 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCONHCH.sub.3                                                                  H                                                 595 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCSNHCH.sub.3                                                                  H                                                 596 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)NH.sub.2                                                                       H                                                 597 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)CN                                                                             H                                                 598 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)CONH.sub.2                                                                     H                                                 599 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCH.sub.2 OCH.sub.3                                                            H                                                 600 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH(CH.sub.3)OCH.sub.2 SCH.sub.3                                                            H                                                 601 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H COCH═CH.sub.2                                                                          H                                                 602 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H COC.tbd.CH  H                                                 603 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H COCH.sub.2 OCH.sub.3                                                                       H                                                 604 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H COCH.sub.2 SCH.sub.3                                                                       H                                                 605 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H C.sub.5 H.sub.11                                                                           H 1.5397                                          606 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR74##  H 109-111                                         607 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR75##  H 1.5389                                          608 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR76##  H                                                 609 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H                                                                                 ##STR77##  H                                                 610 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H CH═CHCH.sub.3                                                                          H 149-151                                         611 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H C(CH.sub.3)═CH.sub.2                                                                   H 155-156                                         612 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H C(CH.sub.3)═CHCH.sub.3                                                                 H 153-155                                         613 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H C(C.sub.2 H.sub.5)═CH.sub.2                                                            H                                                 614 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                           H C(C.sub.2 H.sub.5)═CHCH.sub.3                                                          H                                                 __________________________________________________________________________

                                      TABLE 20                                     __________________________________________________________________________     Comp.                                   m.p. (° C.)                     Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5        RI n.sub.D.sup.20                      __________________________________________________________________________     615 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3)═C(CH.sub.3).sub.2                                                       H                                                     616 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH═C(CH.sub.3).sub.2                                                                H                                                     617 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CH.sub.2 Br    181-183                                618 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CH.sub.2 CN    224-226                                619 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CH.sub.2 CONH.sub.2                                                                           127-129                                620 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCHF.sub.2                                            621 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCH.sub.2 CH═CH.sub.2                             622 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCH.sub.2 C.tbd.CH                                                                            1.5331                                 623 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCH.sub.2 COOCH.sub.3                                                                         53-55                                  624 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 OCH(CH.sub.3)COOCH.sub.3                                                                      71-73                                  625 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 SCHF.sub.2                                            626 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 SCH.sub.2 CH═CH.sub.2                             627 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 SCH.sub.2 C.tbd.CH                                    628 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 SCH.sub.2 COOC.sub.2 H.sub.5                          629 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 SCH(CH.sub.3)COOCH.sub.3                              630 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR78##     1.5275                                 631 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CSCH.sub.3     1.5967                                 632 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR79##     1.5331                                 633 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR80##                                            634 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COOCH.sub.2 CH.sub.2 F                                                                        109-110                                635 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CH═CH.sub.2                                                                               58-60                                  636 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 CH═CHCH.sub.3                                                                             1.5409                                 637 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR81##                                            638 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3                                                                                 ##STR82##     169-170                                639 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         COCH.sub.2 Br  158-159                                640 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         COOC.sub.2 H.sub.5                                                                            1.5140                                 641 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         COOC.sub.5 H.sub.11                                                                           1.5209                                 642 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                          ##STR83##     1.5485                                 643 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9                                                                         CHO            128-130                                644 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9                                                                         COOCH.sub.3    1.5410                                 645 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9                                                                         COOH           1.5342                                 __________________________________________________________________________

                                      TABLE 21                                     __________________________________________________________________________     Comp.                          m.p. (° C.)                              Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5                                                                              RI n.sub.D.sup.20                               __________________________________________________________________________     646 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9 --i                                                                     CHO   54-55                                           647 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9 --i                                                                     COOCH.sub.3                                                                          62-63                                           648 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.4 H.sub.9 --i                                                                     COOH  208-209                                         649 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.5 H.sub.11                                                                        CHO   Unmeasurable                                    650 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.5 H.sub.11                                                                        COOCH.sub.3                                                                          1.5271                                          651 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.5 H.sub.11                                                                        COOH  1.5156                                          652 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Br                                                                             CH.sub.2 Br                                                                          225-227                                         653 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Br                                                                             CHBr.sub.2                                                                           146-147                                         654 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H NO.sub.2 CH.sub.3                                                                             146-148                                         655 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H H        COOCH.sub.3                                                                          95-97                                           656 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              COOCH.sub.3                                                                          91-93                                           657 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                          COOCH.sub.3                                                                          95-97                                           658 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)OH                                                                   COOCH.sub.3                                                                          142-145                                         659 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Br                                                                             COOC.sub.2 H.sub.5                                                                   1.5535                                          660 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SCH.sub.3                                                                      COOC.sub.2 H.sub.5                                                                   103-105                                         661 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 CH.sub.3                                                              COOC.sub.2 H.sub.5                                                                   73-75                                           662 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 SO.sub.2 CH.sub.3                                                     COOC.sub.2 H.sub.5                                                                   182-183                                         663 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SC.sub.2 H.sub.5                                                               COOC.sub.2 H.sub.5                                                                   1.5481                                          664 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5                                                       COOC.sub.2 H.sub.5                                                                   57-59                                           665 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHBr.sub.2                                                                              COOC.sub.2 H.sub.5                                                                   112-114                                         666 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CHO      COOC.sub.2 H.sub.5                                                                   Unmeasurable                                    667 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                          COOC.sub.2 H.sub.5                                                                   1.5378                                          668 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              COOC.sub.2 H.sub.5                                                                   1.5466                                          669 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)Br                                                                          COOC.sub.2 H.sub.5                                                                   1.5300                                          670 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)Cl                                                                          COOC.sub.2 H.sub.5                                                                   Unmeasurable                                    671 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)CN                                                                          COOC.sub.2 H.sub.5                                                                   1.5348                                          672 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H H        COOC.sub.2 H.sub.5                                                                   1.5468                                          673 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 Cl                                                                             CH.sub.2 Cl                                                                          202-203                                         674 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SCH.sub.3                                                                      CH.sub.2 SCH.sub.3                                                                   115-116                                         675 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.2 SO.sub.2 CH.sub.3                                                              CH.sub.2 SO.sub.2 CH.sub.3                                                           169-171                                         676 F F CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              H     204-205                                         677 F F CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                       H     136-137                                         678 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCH.sub.3                                                                   H     1.5220                                          __________________________________________________________________________

                                      TABLE 22                                     __________________________________________________________________________     Comp.                        m.p. (° C.)                                Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5                                                                            RI n.sub.D.sup.20                                 __________________________________________________________________________     679 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OC.sub.2 H.sub.5                                                            H                                                     680 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.2 H.sub.5)OH                                                                  H   137-138                                           681 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)OH                                                                   H   1.5090                                            682 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.3                                                                   H   1.5415                                            683 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCH.sub.3                                                                  H                                                     684 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.3                                                           H   79-80                                             685 F F CH.sub.3                                                                          CF.sub.3                                                                          H C(CH.sub.3).sub.2 SO.sub.2 CH.sub.3                                                     H   108-111                                           686 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.2 H.sub.5                                                            H   1.5345                                            687 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.2 H.sub.5                                                           H                                                     688 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5                                                    H   72-73                                             689 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.3                                                            H                                                     690 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOCH.sub.3                                                           H   1.5251                                            691 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3                                                    H   1.5170                                            692 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SC.sub.2 H.sub.5                                                     H   1.5339                                            693 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOC.sub.2 H.sub.5                                                    H   1.5325                                            694 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 C.sub.2 H.sub.5                                             H   1.5250                                            695 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)CN                                                                          H                                                     696 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)CONH.sub.2                                                                  H                                                     697 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SH                                                                          H                                                     698 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 H   136-137                                           699 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         H   148-149                                           700 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         H   114-115                                           701 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7 --i                                                                     H   1.5435                                            702 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COCH.sub.3                                                                         1.5542                                            703 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         COCH.sub.3                                                                         1.5495                                            704 Cl                                                                               Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         COCH.sub.3                                                                         1.5487                                            705 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H H        H   137-138                                           706 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 H   182-184                                           707 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         H   145-147                                           708 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         H   1.5552                                            709 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              H   187-189                                           710 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H COC.sub.2 H.sub.5                                                                       H   124-125                                           711 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                          H   144-146                                           __________________________________________________________________________

                                      TABLE 23                                     __________________________________________________________________________     Comp.                        m.p. (° C.)                                Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4  R.sup.5                                                                            RI n.sub.D.sup.20                                 __________________________________________________________________________     712 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)OH                                                                   H   1.5420                                            713 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCH.sub.3                                                                   H   1.5322                                            714 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OC.sub.2 H.sub.5                                                            H                                                     715 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.3                                                                   H                                                     716 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCH.sub.3                                                                  H   88-90                                             717 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 H.sub.3                                                            H   107-109                                           718 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SC.sub.2 H.sub.5                                                            H                                                     719 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOC.sub.2 H.sub.5                                                           H   1.5561                                            720 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 C.sub.2 H.sub.5                                                    H   1.5382                                            721 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.3                                                            H                                                     722 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOCH.sub.3                                                           H                                                     723 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3                                                    H                                                     724 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3 COCH.sub.3                                                                         1.5500                                            725 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         COCH.sub.3                                                                         1.5460                                            726 F Br                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         COCH.sub.3                                                                         1.5408                                            727 F H CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         H   129-130                                           728 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H H        H                                                     729 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH.sub.3 H                                                     730 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         H   145-147                                           731 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         H                                                     732 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                          H                                                     733 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.3                                                                   H                                                     734 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.3                                                           H                                                     735 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.3                                                            H                                                     736 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 H.sub.3                                                     H                                                     737 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCH.sub.3                                                                   H                                                     738 F Cl                                                                               NH.sub.2                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              H                                                     739 F F NH.sub.2                                                                          CF.sub.3                                                                          H H        H                                                     740 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH.sub.3 H                                                     741 F F NH.sub.2                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                         H                                                     742 F F NH.sub.2                                                                          CF.sub.3                                                                          H C.sub.3 H.sub.7                                                                         H                                                     743 F F NH.sub.2                                                                          CF.sub.3                                                                          H COCH.sub.3                                                                              H                                                     744 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OH                                                                          H                                                     __________________________________________________________________________

                                      TABLE 24                                     __________________________________________________________________________     Comp.                           m.p. (° C.)                             Nos.                                                                               X Y R.sup.1                                                                           R.sup.2                                                                           R.sup.3                                                                          R.sup.4     R.sup.5                                                                            RI n.sub.D.sup.20                              __________________________________________________________________________     745 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.3                                                                      H                                                  746 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.3                                                              H                                                  747 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.3                                                               H                                                  748 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 CH.sub.3                                                       H                                                  749 F F NH.sub.2                                                                          CF.sub.3                                                                          H CH(CH.sub.3)OCH.sub.3                                                                      H                                                  750 Cl                                                                               F CH.sub.3                                                                          CF.sub.3                                                                          H C.sub.2 H.sub.5                                                                            H   Unmeasurable                                   751 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH.sub.3    NHOH                                                                               107-109                                        752 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCH.sub.2 CF.sub.3                                                             H   1.5351                                         753 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SOCH.sub.2 CF.sub.3                                                            H   73-75                                          754 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SO.sub.2 CH.sub.2 CF.sub.3                                                     H   128-129                                        755 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SCH.sub.2 CF.sub.3                                                      H                                                  756 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SOCH.sub.2 CF.sub.3                                                     H                                                  757 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)SO.sub.2 CH.sub.2 CF.sub.3                                              H   Unmeasurable                                   758 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)SCH.sub.2 CF.sub.3                                                      H                                                  759 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)SOCH.sub.2 CF.sub.3                                                     H                                                  760 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)SO.sub.2 CH.sub.2 CF.sub.3                                              H                                                  761 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.tbd.CH)SCH.sub.2 CF.sub.3                                                             H                                                  762 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.tbd.CH)SOCH.sub.2 CF.sub.3                                                            H                                                  763 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.tbd.CH)SO.sub.2 CH.sub.2 CF.sub.3                                                     H                                                  764 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)OCH.sub.3                                                               H   1.5158                                         765 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.2)OCH.sub.2 CF.sub.3                                                             H   1.5165                                         766 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.2)OCH.sub.2 CH.sub.2 F                                                           H   1.5312                                         767 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH═CH.sub.2)OCH.sub.2 CF.sub.3                                                      H                                                  768 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.tbd.CH)OCH.sub.2 CF.sub.3                                                             H                                                  769 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)OCH.sub.2 CF.sub.3                                                      H                                                  770 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CH(CH.sub.3)SCSN(C.sub.2 H.sub.5).sub.2                                                    H   1.5537                                         771 F F CH.sub.3                                                                          CF.sub.3                                                                          H CH(C.sub.2 H.sub.5)OCH.sub.3                                                               H   1.5216                                         772 F Cl                                                                               CH.sub.3                                                                          CF.sub.3                                                                          H CBr.sub.2 C.sub.2 H.sub.5                                                                  H   197-199                                        __________________________________________________________________________

Now, common processes for producing the compounds of the present invention will be described.

Process 1

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is an alkyl group, a cycloalkyl group or a benzyl group which may be substituted, and R⁵ is a hydrogen atom, an alkyl group, a benzyl group which may be substituted, or a phenyl group which may be substituted, can be produced as follows. ##STR84## (In the formulae, each of R¹, R², R³, X and Y is as defined above, L represents a leaving group, each of R¹² and R¹³ is a hydrogen atom, an alkyl group or a phenyl group which may be substituted, or R¹² and R¹³ are mutually connected to represent a carbon ring, and R¹⁴ is a hydrogen atom, an alkyl group, a benzyl group which may be substituted, or a phenyl group which may be substituted.)

The compound (A-2) can be obtained by a known method (Synthesis, 1981, 1-28) wherein the compound (A-1) is reacted with the propargyl alcohol derivative in the presence of an azo compound and triphenylphosphine, or by a conventional method wherein it is condensed with the propargyl derivative containing the leaving group in the presence of a base. Further, the compound (A-3) can be produced by cyclizing the compound (A-2) in a solvent in the presence of a base.

Here, as the solvent, an aromatic hydrocarbon such as toluene, xylene or mesitylene, an ether such as 1,4-dioxane or tetrahydrofuran, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, an aromatic nitrogen-containing compound such as quinoline or pyridine, or an aniline derivative such as N,N-diethylaniline or N,N-dimethylaniline, may be mentioned. Especially for the ring closure reaction of the compound (A-2), N,N-diethylaniline is preferred. Further, as the azo compound, diethyl azodicarboxylate is preferred. As the base, a hydride, hydroxide, carbonate, hydrogencarbonate or organic acid salt of an alkali metal or an alkaline earth metal, a metal fluoride compound such as cesium fluoride or potassium fluoride, or an organic base such as triethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene or pyridine, may be mentioned. The reaction can be carried out at a temperature from ice temperature to the refluxing temperature of the solvent.

Process 2

Among compounds represented by the general formula (1), compounds (B-7) and (C-3) of the present invention wherein R¹ is a hydrogen atom, can be produced as follows. ##STR85## (In the formulae, each of R², R³, R⁴, R⁵. R¹², R¹³, R¹⁴, X and Y, is as defined above, R¹⁵ is an alkyl group, a phenyl group which may be substituted, or a benzyl group which may be substituted, and PN represents an amino group having a protecting group such as a mono- or di-acylamino group, a mono- or di-haloalkylcarbonylamino group, a mono- or di-alkylsulfonylamino group, a mono-or di-haloalkylsulfonylamino group, a tetrahydrophthalimino group or a phthalimino group.)

The compound (B-2) can be produced by ring-closing the compound (B-1) in the same manner as in the method described in Process 1. Then, the compound (B-2) is converted to the compound (B-3) in accordance with e.g. the after-mentioned processes (Processes 5 to 35) for producing uracil derivatives or a method disclosed in a literature (Methoden del Organitien Chemie, vol. E6b1, p.33-162, 1994), and its protecting group is removed to produce the aniline compound (B-4). The aniline compound (B-4) is reacted with e.g. phenyl chlorocarbonate by a conventional method to obtain a carbamate compound (B-5), which is then reacted with the compound (B-6), whereupon the product is subjected to acid treatment to obtain the desired compound (B-7).

Otherwise, the aniline compound (C-1) can be produced by removing the protecting group of the compound (B-2). The aniline compound (C-1) is reacted with e.g. phosgene to obtain a compound (C-2), or it is reacted with e.g. phenyl chlorocarbonate to obtain a compound (C-4), and then these compounds are, respectively, reacted with the compound (B-6), whereupon the obtained products are subjected to acid treatment to obtain the desired compound (C-3).

A method for removing the protecting group P may be by means of hydrolysis in the presence of a base, or in a case where the protecting group is a tetrahydrophthalimino group or a phthalimino group, it can be removed by reacting with hydrazine.

Production of the compound (B-5) or the compound (C-4), is carried out usually by a reaction in a solvent in the presence of a base at a reaction temperature of from 0 to 120° C., preferably from 20 to 80° C. for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 2 equivalents of the chlorocarbonate derivative and from 1 to 1.5 equivalents of the base, per equivalent of the compound (B-4) or the compound (C-1). As the base, an inorganic base such as potassium carbonate or sodium hydride, or an organic base such as triethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene or pyridine, may be mentioned. As the solvent, an ether such as diethyl ether or tetrahydrofuran, a halogenated hydrocarbon such as chloroform or carbon tetrachloride, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, an aromatic hydrocarbon such as benzene or toluene, or a mixture thereof, may be mentioned.

Production of the compound (C-2) is carried out usually by a reaction in a solvent at a reaction temperature of from 0 to 120° C., preferably from 20 to 100° C., for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 2 to 10 equivalents of phosgene and from 1 to 1.5 equivalents of the base, per equivalent of the compound (C-1). As the solvent, a halogenated hydrocarbon such as chloroform or carbon tetrachloride, an aromatic hydrocarbon such as benzene or toluene, an aliphatic hydrocarbon such as hexane or heptane, or a mixture thereof, may be mentioned.

Production of the compound (B-7) from the compound (B-5), or production of the compound (C-3) from the compound (C-4), is carried out usually by a reaction in a solvent in the presence of a base at a reaction temperature of from 0 to 150° C., preferably from 20 to 120° C., for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 10 equivalents of the compound (B-6) and from 1 to 10 equivalents of the base, per equivalent of the compound (B-5) or the compound (C-4). As the base, an inorganic base such as potassium hydride or sodium hydride, or an organic base such as 1,8-diazabicyclo[5.4.0]-7-undecene, may be mentioned. As the solvent, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon such as benzene or toluene, an aliphatic hydrocarbon such as hexane or heptane, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, or a mixture thereof, may be mentioned.

Production of the compound (C-3) from the compound (C-2) is carried out usually by a reaction in a solvent in the presence of a base at a reaction temperature of from 0 to 60° C., preferably from 5 to 30° C., for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 1.5 equivalents of the compound (B-6) and from 1 to 1.5 equivalents of the base, per equivalent of the compound (C-2). As the base, an inorganic base such as potassium hydride or sodium hydride, may, for example, be mentioned. As the solvent, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon such as benzene or toluene, an aliphatic hydrocarbon such as hexane or heptane, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, or a mixture thereof, may be mentioned.

The starting material compound (B-1) can be produced as follows. ##STR86## (In the formulae, each of R¹², R¹³, R¹⁴, PN, X and Y is as defined above, R¹⁶ is an alkyl group or a benzyl group which may be substituted, X¹ and Y¹ represent X and Y other than a fluorine atom, respectively, and E is a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyloxy group.)

The compound (D-3) can be produced by reacting the compound (D-1) or the compound (D-2) with the corresponding alkynyl alcohol in the presence of a base. Otherwise, the compound (D-3) can be produced in accordance with the method described in Process 1, after producing the compound (D-9) by hydrolyzing the compound (D-1) or the compound (D-2) in the presence of a base. Then, the obtained (D-3) is reduced to produce the compound (D-4), and then the nitrogen atom is protected by a protecting group, to obtain the compound (B-1).

Further, the compound (D-5) can be produced by reacting the compound (D-1) or the compound (D-2) with the corresponding alcohol in the presence of a base, or by reacting the compound (D-9) with the compound R¹⁶ -E. Then, the compound (D-5) is reduced to obtain the compound (D-6), and then the nitrogen atom is protected by a protecting group, to obtain the compound (D-7). Further, R¹⁶ is removed from the compound (D-7) to obtain the compound (D-8), and then the compound (B-1) can be produced in accordance with the method described in Process 1.

When R¹⁶ is an alkyl group, it can be removed by means of a dealkylating agent such as boron tribromide, and when R¹⁶ is a benzyl group which may be substituted, it can be removed by hydrogenation under atmospheric pressure.

Further, a compound [which corresponds to (D-1)] wherein X is a fluorine atom, and Y is a chlorine atom or a bromine atom, can be produced by chlorinating or brominating the 4-position of the phenyl ring of 2,6-difluoroaniline, with a halogenating agent such as N-chlorosuccinic imide (NCS) or N-bromosuccinic imide (NBS), followed by oxidation with an oxidizing agent such as metachloroperbenzoic acid.

For example, a compound [which corresponds to (D-1)] wherein X is a fluorine atom, and Y is a cyano group, can be produced by oxidizing 2,6-difluoro-4-cyanoaniline, with an oxidizing agent such as metachloroperbenzoic acid.

Process 3

Among compounds represented by the general formula (1), a compound (E-2) or (E-3) of the present invention wherein R¹ is an alkyl group or a haloalkyl group, can be produced as follows. ##STR87## (In the formulae, each of R², R³, R⁴, R⁵, R¹², R¹³, R¹⁴, R¹⁵, E, X and Y, is as defined above, and R¹⁷ is an alkyl group or a haloalkyl group.)

The compound (E-2) can be produced by reacting the compound R¹⁷ -E with the compound (B-7) of the present invention produced by the above Process 2 or with the compound (B-7) of the present invention which corresponds to the compound (A-3) produced by the above Process 1, wherein R¹ is a hydrogen atom, or by reacting the compound (B-5) with the compound (E-1) in accordance with the method shown in Process 2.

Further, the compound (E-3) can be produced by reacting the compound (C-2) with the compound (E-1) in accordance with the method shown in Process 2.

Production of the compound (E-2) from the compound (B-7) is carried out usually by a reaction in a solvent in the presence of a base at a reaction temperature of from 0 to 100° C. for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 10 equivalents of the compound (R¹ -E) and from 1 to 1.5 equivalents of the base, per equivalent of the compound (B-7). As the base, an inorganic base such as potassium carbonate, potassium hydride or sodium hydride, or an alkali metal alkoxide such as sodium ethoxide or sodium methoxide, may, for example, be mentioned. As the solvent, a halogenated hydrocarbon such as chloroform or carbon tetrachloride, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon such as benzene or toluene, an aliphatic hydrocarbon such as hexane or heptane, a ketone such as acetone or methyl isobutyl ketone, an ester such as ethyl acetate, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, or a mixture thereof, may be mentioned.

Process 4

Among compounds represented by the general formula (1), the compound (G-1) of the present invention wherein R¹ is an amino group, can be prepared as follows. ##STR88## (in the formulae, each of R², R3 R⁴, R⁵, X and Y, is as defined above, G is a methanesulfonyloxy group, a p-toluenesulfonyloxy group, or a 2,4-dinitrophenoxy group.)

The compound (G-1) can be prepared by reacting the compound G-NH₂ with the compound (B-7) of the present invention produced by the above Process 2, or with the compound (B-7) of the present invention which corresponds to the compound (A-3) produced by the above Process 1 wherein R¹ is a hydrogen.

This reaction is carried out usually in a solvent in the presence of a base at a reaction temperature of from 0 to 100° C. for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 10 equivalents of the compound (G-NH₂) and from 1 to 1.5 equivalents of the base, per equivalent of the compound (B-7). As the base, an inorganic base such as potassium carbonate, potassium hydride or sodium hydride, or an alkali metal alkoxide such as sodium ethoxide or sodium methoxide, may, for example, be mentioned. As the solvent, a halogenated hydrocarbon such as chloroform or carbon tetrachloride, an ether such as diethyl ether or tetrahydrofuran, an aromatic hydrocarbon such as benzene or toluene, an aliphatic hydrocarbon such as hexane or heptane, a ketone such as acetone or methyl isobutyl ketone, an ester such as ethyl acetate, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane, or a mixture thereof, may be mentioned.

Process 5

Among compounds represented by the general formula (1), a compound of the present invention wherein R4 is a haloalkyl group, can be prepared by reacting a compound represented by the general formula (I-1): ##STR89## (wherein, each of R², R³, R¹², R¹³, X and Y, is as defined above, R¹⁸ is an amino group, an alkyl group or a haloalkyl group, and R¹⁹ is a hydrogen atom, an alkoxy group, a haloalkoxy group, a phenylsulfonyl group which may be substituted, a halogen atom, a phenyl group which may be substituted, a nitro group, an alkoxycarbonyl group or a benzyl group which may be substituted), with a halogenating agent, as a mixture of compounds represented by the general formulae: ##STR90## (wherein each of R¹, R², R³, R¹², R¹³, R¹⁸, R¹⁹, X and Y, is as defined above, and A is a halogen atom). [However, the compound (I-3) can be produced only when R¹³ of the compound (I-1) is a hydrogen atom, and the compound (I-4) can be produced only when R¹² and R¹³ in the compound (I-1) are both hydrogen atoms.] The desired compound can be obtained by isolating and purifying the mixture of these compounds.

This reaction is carried out in a solvent in the presence or absence of a catalyst at a reaction temperature of from 0 to 150° C., preferably from 30 to 100° C., for from 0.5 to 24 hours. The amounts of the reagents used for the reaction are from 1 to 10 equivalents of the halogenating agent and from 0.01 to 0.5 equivalent of the catalyst, per equivalent of the compound (I-1). As the halogenating agent, a halogen such as bromine or chlorine, an N-halosuccinic imide such as N-bromosuccinic imide, or a pyridine salt such as pyridinium perbromide, may, for example, be mentioned. As the solvent, a halogenated hydrocarbon such as chloroform or carbon tetrachloride, a carboxylic acid such as formic acid or acetic acid, an amide such as N,N-dimethylformamide, or a sulfur compound such as dimethylsulfoxide or sulfolane, may, for example, be mentioned. As the catalyst, benzoyl peroxide, α, α'-azobisisobutyronitrile, or a mixture thereof, may be mentioned.

Process 6

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a formyl group, can be prepared by hydrolyzing a compound which is the compound (I-3) produced by the above Process 5 wherein R¹² is a hydrogen atom, by a conventional method.

Process 7

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a carboxyl group, can be prepared by hydrolyzing the compound (I-4) produced by the above Process 5, or by oxidizing a compound of the present invention wherein R⁴ is a formyl group, produced by the above Process 6, with an oxidizing agent such as a Jones' reagent (a mixed solution comprising chromium trioxide, sulfuric acid and water; see Organic Syntheses col. Vol. 1).

Process 8

Among compounds represented by the general formula (I), a compound of the present invention wherein R⁴ is a hydrogen atom, can be prepared by decarboxylating the compound of the present invention wherein R⁴ is a carboxyl group, produced by the above Process 7, in the presence of a copper catalyst.

Process 9

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --COR²⁰, can be prepared by subjecting the compound wherein R⁴ is a hydrogen atom, produced by the above Process 8 and the corresponding acid anhydride (R²⁰ CO)₂ O or acid halide R²⁰ COL¹, to a Friedel Crafts reaction in the presence of a Lewis acid. (In the formulae, R²⁰ is an alkyl group, a cycloalkyl group, a haloalkyl group or a phenyl group which may be substituted, and L¹ is a chlorine atom, a bromine atom or an iodine atom.)

Further, a compound of the present invention wherein R⁴ is a group of --COR¹², can be produced by hydrolyzing the compound (I-3) produced by the above Process 5 wherein R¹² is an alkyl group or a phenyl group which may be substituted, in the same manner as in Process 6.

Process 10

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a hydroxyiminoalkyl group, a hydroxyiminohaloalkyl group, an alkoxyiminoalkyl group or an alkoxyiminohaloalkyl group, can be prepared by reacting a compound of the present invention wherein R⁴ is an acyl group or a haloalkylcarbonyl group, produced by the above Process 6 or 9, with a compound represented by the general formula NH₂ OR²¹ (wherein R²¹ is a hydrogen atom or an alkyl group) or its sulfate or hydrochloride.

Process 11

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a hydrazonoalkyl group, an alkylhydrazonoalkyl group, a phenylhydrazonoalkyl group which may be substituted, an alkyliminoalkyl group or a phenyliminoalkyl group which may be substituted, can be prepared by reacting a compound of the present invention wherein R⁴ is an acyl group, produced by the above Process 6 or 9, with a compound represented by the general formula NH₂ NR²² (R²³) (wherein each of R²² and R²³ which are the same or different, is a hydrogen atom, an alkyl group or a phenyl group which may be substituted), or its sulfate or hydrochloride.

Process 12

Among compounds represented by the general formula (1), a compound of the present invention wherein R4 is a cyano group, can be prepared by dehydrating a compound of the present invention wherein R⁴ is a hydroxyiminomethyl group, produced by the above Process 10, in the presence of an acid catalyst such as p-toluenesulfonic acid.

Process 13

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)OH, can be prepared by reacting a compound of the present invention wherein R⁴ is a group of --COR⁶, produced by the above Process 6 or 9, with a Grignard reagent R⁷ MgL¹. (In the formulae, R⁶, R⁷ and L¹ are as defined above.)

Process 14

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --COR⁷, can be prepared by oxidizing a compound of the present invention wherein R⁴ is a group of --CH(R⁷)OH, produced by the above Process 13, with e.g. a Jones' reagent. (In the formulae, R⁷ is as defined above.)

Process 15

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --CH(R⁷)OH, can be prepared by reducing a compound of the present invention wherein R⁴ is a group of --COR⁷, produced by the above Process 6, 9 or 14, with a reducing agent such as diisobutylaluminum hydride. (In the formulae, R⁷ is as defined above.)

Process 16

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)L¹, can be prepared by halogenating a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)OH, produced by the above Process 13, with a halogenating agent such as [triphenylphosphine/chloranil(tetrachlorobenzoquinone)]. (In the formulae, R⁶, R⁷ and L¹ are as defined above.)

Process 17

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)ZR⁹ or a group of --C(R⁶) (R⁷)N(R⁶)R²⁴, can be prepared by reacting the compound (I-2) produced by the above Process 5 or the compound produced by the above Process 16, with a compound represented by the general formula R⁹ SH, R⁹ OH or R⁶ (R²⁴)NH (wherein each of R⁶, R⁷, R⁹ and Z, is as defined above, and R²⁴ is a hydrogen atom or an alkyl group). This reaction is carried out in a solvent in the presence or absence of a base at a reaction temperature of from 0 to 100° C., preferably from 20 to 80° C. for from 0.5 to 24 hours. As the solvent to be used for this reaction, an ether such as diethyl ether or tetrahydrofuran, an amide such as N,N-dimethylformamide, a sulfur compound such as dimethylsulfoxide or sulfolane or an aromatic hydrocarbon such as benzene or toluene, may be mentioned. As the base, a metal hydride such as sodium hydride or potassium hydride, potassium carbonate, or sodium methoxide, may, for example, be mentioned.

Process 18

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶)(R⁷)WR⁹, can be prepared by oxidizing a compound wherein R⁴ is a group of --C(R⁶) (R⁷)SR⁹, produced by the above Process 16, with an oxidizing agent such as metachloroperbenzoic acid or potassium peroxymonosulfate (tradename: Oxone). (In the formulae, each of R⁶, R⁷, R⁹ and W is as defined above.)

Process 19

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --COOR²⁵, can be prepared by reacting a compound wherein R⁴ is a carboxyl group, produced by the above Process 7, with a compound represented by the general formula R²⁵ OH, in the presence of an acid catalyst, or by reacting it with a compound represented by the general formula R²⁶ -L¹, in the presence of a base. (In the formulae, L¹ is as defined above, R²⁵ is an alkyl group, a haloalkyl group, a benzyl group which may be substituted, or a phenyl group which may be substituted, and R²⁶ is an alkyl group, a haloalkyl group, or a benzyl group which may be substituted.)

Process 20

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a carbamoyl group (having the same or different hydrogen atoms, alkyl groups or phenyl groups which may be substituted, substituted on the nitrogen atom), can be prepared by reacting a compound of the present invention wherein R⁴ is a carboxyl group, produced by the above Process 7, with thionyl chloride, and then reacting it with a compound represented by the general formula R²⁷ (R²⁸)NH (wherein each of R²⁷ and R²⁸ which may be the same or different, is a hydrogen atom, an alkyl group or a phenyl group which may be substituted).

Process 21

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)SH, can be prepared by reacting the compound (I-2) produced by the above Process 5 or a compound of the present invention produced by the above Process 16 wherein R is a group of --C(R⁶)(R⁷) L¹, with a thiol-modifying agent such as sodium sulfide or sodium hydrogensulfide in the presence of a base, followed by acid treatment. (In the formulae, R⁶, R⁷ and L¹ are as defined above.)

Process 22

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)ZR⁸, can be prepared by reacting a compound of the present invention wherein R⁴ is a group of --CH(R⁷)OH, produced by the above Process 15, a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)OH, produced by the above Process 13, or a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)SH, produced by the above Process 21, with a compound represented by the general formula R²⁹ -E or with a compound represented by the general formula R³⁰ N═C═Z, in the presence of a base. (In the formulae, R⁶, R⁷, R⁸, Z and E are as defined above, R²⁹ is an alkyl group, a cycloalkyl group, haloalkyl group, an alkoxycarbonylalkyl group, a hydroxycarbonylalkyl group, a monoalkylcarbamoylalkyl group, a dialkylcarbamoylalkyl group, an acyl group, an alkylsulfonyl group, a haloalkylsulfonyl group, a haloalkylcarbonyl group, a dialkylcarbamoyl group, a dialkylthiocarbamoyl group or a benzoyl group which may be substituted, and R³⁰ is an alkyl group.)

Process 23

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)N(R⁶)R³¹, can be prepared by reacting a compound of the present invention wherein R⁴ is a group of --C(R⁶) (R⁷)NH(R⁶), produced by the above Process 17, with a compound represented by the general formula R³¹ -E, in the presence of a base. (In the formulae, R⁶, R⁷ and E are as defined above, and R³¹ is an alkyl group, an acyl group, an alkylsulfonyl group, a haloalkylsulfonyl group, or a haloalkylcarbonyl group.)

Process 24

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁵ is a group of --COR²⁰, can be prepared by subjecting a compound of the present invention wherein R⁵ is a hydrogen atom and a corresponding acid hydride R²⁰ COL¹, to a Friedel Crafts reaction in the presence of a Lewis acid. (In the formulae, R²⁰ and L¹ are as defined above.)

Process 25

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁵ is a formyl group, can be prepared by e.g. a known method [Jikken Kagaku Kouza (4th edition), vol. 21, p. 110] which comprises reacting a compound of the present invention wherein R⁵ is a hydrogen atom, with a dichloromethylalkyl ether in the presence of a Lewis acid.

Using compounds of the present invention wherein R⁵ is an alkyl group, which can be produced by the above Processes 1 to 4, or compounds of the present invention wherein R⁵ is an acyl group, which can be prepared by the above Process 24 or 25, as starting materials, compounds of the present invention having various substituents for R⁵ can be prepared in the same manner as for R⁴, in accordance with any suitable processes described in the foregoing.

Process 26

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a group of --CSR²⁰, can be prepared by thiocarbonyl-modifying a compound of the present invention wherein R⁴ or R⁵ is a group of --COR²⁰, produced by the above process, with e.g. phosphorous pentasulfide, a Lawesson's reagent [(2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphethane-2,4-disulfide]. (In the formulae, R²⁰ is as defined above.)

Process 27

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a halogen atom, can be prepared by halogenating a compound of the present invention wherein R⁴ or R⁵ is a hydrogen atom, produced by the above process, with a halogenating agent such as bromine.

Process 28

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a nitro group, can be prepared by nitration of a compound of the present invention wherein R⁴ or R⁵ is a hydrogen atom, produced by the above process, by a conventional method.

Process 29

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a cyanoalkyl group, can be prepared by cyano-modifying a compound of the present invention wherein R⁴ or R⁵ is a haloalkyl group, produced by the above process, with a cyano-modifying agent such as potassium cyanide.

Process 30

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a carbamoylalkyl group, can be prepared by hydrolyzing a cyano group of a compound of the present invention wherein R⁴ or R⁵ is a cyanoalkyl group, produced by the above Process 29, under an acidic or basic condition.

Process 31

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a thiocyanatealkyl group, can be prepared by thiocyanate-modifying a compound of the present invention wherein R⁴ or R⁵ is a haloalkyl group, produced by the above process, with a thiocyanate-modifying agent such as potassium thiocyanate.

Process 32

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is a group of --CR³² ═CR³³ R³⁴, can be prepared by a Witig reaction which comprises reacting a compound of the present invention wherein R⁴ or R⁵ is an acyl group of --COR³², produced by the above process, with a phosphonium reagent [Ph₃ P³⁰ CHR³³ R³⁴ ]L¹⁻, in the presence of a base. (L¹ is as defined above, and each of R³², R³³ and R³⁴ which are the same or different, is a hydrogen atom or an alkyl group, and Ph₃ P represents a triphenylphosphine.)

Process 33

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁴ or R⁵ is an oxiranyl group which may be substituted by an alkyl group, can be prepared by oxidizing a compound of the present invention wherein R⁴ or R⁵ is a group of --CR³² ═CR³³ R³⁴, produced by the above Process 32, with an oxidizing agent such as metachloroperbenzoic acid. (Each of R³², R³³ and R³⁴ is as defined above.)

Process 34

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁵ is an alkoxy group, a haloalkoxy group, an alkenyloxy group, an alkynyloxy group or an alkoxycarbonylalkoxy group, can be produced by reacting a compound wherein R⁵ is a hydroxyl group, with a compound represented by the general formula R³⁵ -E (wherein E is as defined above, and R³⁵ is an alkyl group, an alkenyl group, an alkynyl group, an alkoxycarbonylalkyl group or a haloalkyl group) in the presence of a base. Further, the compound wherein R⁵ is a hydroxyl group, can be prepared by reacting a compound of the present invention wherein R⁵ is a nitro group, produced by the above process, with iron in the presence of e.g. an acetic acid catalyst in a solvent mixture of toluene-water.

Process 35

Among compounds represented by the general formula (1), a compound of the present invention wherein R⁵ is a hydroxyamino group, can be prepared by reducing a compound of the present invention wherein R⁵ is a nitro group, produced by the above process, with iron in the presence of e.g. an acetic acid catalyst in a solvent mixture of ethyl acetate-water.

Further, the compound (A-1) as the starting material in Process 1, can be produced as follows. ##STR91## (In the formulae, each R¹, R², R³, R¹⁵, R¹⁶, E, G, X and Y, is as defined above, and R¹⁷ is an alkyl group or a haloalkyl group.)

The compound (J-1) or (J-2) is prepared from the compound (D-6) in accordance with the above Process 2, and then reacted with the compound (B-6) to obtain the compound (J-3). Further, in a case where R¹ is an alkyl group or a haloalkyl group, the compound (J-3) is reacted with a compound represented by the general formula R¹⁷ -E in the presence of a base, in accordance with the above Process 3, to obtain the compound (J-4), or in a case where R¹ is an amino group, the compound (J-3) is reacted with a compound represented by the general formula G-NH₂ in the presence of a base, in accordance with the above Process 4 to obtain the compound (J-4). The compound (J-4) is reacted with a dealkylating agent such as boron tribromide in a case where R¹⁶ is an alkyl group, or it is hydrogenated under atmospheric pressure in a case where R¹⁶ is a benzyl group which may be substituted, to obtain the compound (A-1).

Best Mode for Carrying out the Invention

Now, specific Preparation Examples will be described.

PREPARATION EXAMPLE 1 Preparation of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 2)

100 ml of N,N-diethylaniline was added to 5.2 g (14 mmol) of 3-(4-chloro-2-fluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 6.4 g (42 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.4 g (yield: 26.9%) of the desired product as white powder. Melting point: 196-197° C.

PREPARATION EXAMPLE 2 Preparation of 3-(4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 196)

200 ml of N,N-diethylaniline was added to 20.0 g (55.8 mmol) of 3-(4-chloro-2-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 17.0 g (112 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 7.0 g (yield: 35.0%) of the desired product as white crystals. Melting point: 206-207° C.

PREPARATION EXAMPLE 3 Preparation of 3-(4-chloro-2,3-dimethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 265)

2.0 g (6.2 mmol) of 3-(4-chloro-2-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil and 1.3 g (7.5 mmol) of diethyl azodicarboxylate, were dissolved in 30 ml of tetrahydrofuran, and 20 ml of a tetrahydrofuran solution containing 2.0 g (7.6 mmol) of triphenylphosphine and 0.52 g (9.3 mmol) of 2-butyne-1-ol, was dropwise added thereto under cooling with ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes to obtain an ether compound. Then, 20 ml of N,N-diethylaniline was added to the purified ether compound and 0.94 g (6.2 mmol) of cesium fluoride, followed by heating at 190° C. for 15 hours. After completion of the reaction, the reaction mixture was purified by silica gel column chromatography to obtain 0.52 g (yield: 22.4%) of the desired product as white crystals. Melting point: 152-153° C.

PREPARATION EXAMPLE 4 Preparation of 3-(4,6-difluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 375)

100 ml of N,N-diethylaniline was added to 4.7 g (13 mmol) of 3-(2,4-difluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil and 5.9 g (39 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.0 g (yield: 21.3%) of the desired product as white powder. Melting point: 176-178° C.

PREPARATION EXAMPLE 5 Preparation of 3-(4-chloro-2-ethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 197)

50 ml of N,N-diethylaniline was added to 1.25 g (3.4 mmol) of 3-[4-chloro-2-(1-methyl-2-propynyloxy)phenyl]-1-methyl-6-trifluoromethyluracil and 1.0 g (6.8 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 30 minutes. After completion of the reaction, the reaction mixture was purified directly by silica gel column chromatography to obtain 0.60 g (yield: 50.7%) of the desired product as white crystals. Melting point: 159-160° C.

PREPARATION EXAMPLE 6 Preparation of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil (Compound No. 187)

80 ml of N,N-dimethylformamide was added to 5.8 g (32 mmol) of ethyl 3-amino-4,4,4-trifluorocrotonate and 6.6 g (43 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene, and 9.6 g (29 mmol) of 4-chloro-2-ethyl-6-fluoro-7-phenoxycarbonylaminobenzofuran was gradually added thereto at room temperature. After stirring at 60° C. for 8 hours, the reaction solution was poured into a 10% hydrochloric acid aqueous solution and acidified, and then extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 4.8 g (yield: 44%) of the desired product as white crystals. Melting point: 154-155° C.

PREPARATION EXAMPLE 7 Preparation of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 3)

0.50 g (1.3 mmol) of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil and 0.30 g (2.3 mmol) of potassium carbonate, were suspended in 20 ml of N,N-dimethylformamide, and 0.23 g (1.6 mmol) of methyl iodide was dropwise added thereto under cooling with ice. After stirring at room temperature for 3 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.48 g (yield: 92%) of the desired product as white crystals. Melting point: 142-143° C.

PREPARATION EXAMPLE 8 Preparation of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-1-amino-6-trifluoromethyluracil (Compound No. 730)

80 ml of N,N-dimethylformamide was added to 3.4 g (9.0 mmol) of 3-(4-chloro-2-ethyl-6-fluorobenzofuran-7-yl)-6-trifluoromethyluracil, 2.7 g (14 mmol) of 2,4-dinitrophenoxyamine and 5.0 g (36 mmol) of potassium carbonate, followed by stirring at 60 to 70° C. for 1 hour. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.0 g (yield: 58%) of the desired product as white crystals. Melting point: 145-147° C.

PREPARATION EXAMPLE 9 Preparation of 3-(2-bromomethyl-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (A, Compound No. 8), 3-(4-chloro-2-dibromomethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (B, Compound No. 9) and 3-(4-chloro-6-fluoro-2-tribromomethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (C, Compound No. 10)

400 ml of carbon tetrachloride was added to 20.0 g (53.1 mmol) of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, 56.8 g (319.1 mmol) of N-bromosuccinimide, 0.2 g (1.4 mmol) of benzoyl peroxide and 0.2 g (1.2 mmol) of α, α'-azobisisobutyronitrile, followed by stirring for 24 hours under heating and refluxing. After completion of the reaction, the reaction solution was cooled, and precipitated crystals were filtered off. The filtrate was washed sequentially with an aqueous sodium hydrogensulfite, water and a saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The obtained residue was separated by silica gel column chromatography to obtain 5.0 g (yield: 20.6%) of (A) as white crystals, melting point: 168-172° C., 12.0 g (yield: 42.3%) of (B) as white crystals, melting point: 126-128° C. and 0.6 g (yield: 1.8%) of (C) as a dark brown viscous liquid, refractive index: unmeasurable, respectively. ¹ H-NMR of Compound No. 10 (solvent, CDCl₃): 3.61 (3H,bs), 6.42(1H,s), 7.26(1H,d)ppm.

PREPARATION EXAMPLE 10 Preparation of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 33)

60 ml of concentrated sulfuric acid was added to 12.0 g (22.5 mmol) of 3-(4-chloro-2-dibromomethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, followed by stirring at 50° C. for 1 hour. After completion of the reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution, water and a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was crystallized from isopropyl ether to obtain 7.6 g (yield: 88.4%) of the desired product as pale yellow crystals. Melting point: 180-183° C.

PREPARATION EXAMPLE 11 Preparation of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 42)

10 ml of concentrated sulfuric acid was added to 0.6 g (0.98 mmol) of 3-(4-chloro-6-fluoro-2-tribromomethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, followed by stirring at 45° C. for 3 hours. After completion of the reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.21 g (yield: 53.7%) of the desired product as white crystals. Melting point: 267-268° C. (decomposed).

PREPARATION EXAMPLE 12 Preparation of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 42)

1.5 g (3.84 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 20 ml of acetone, and a Jones' reagent was dropwise added thereto at 5° C. until the orange color no longer disappeared. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 76.9%) of the desired product as white crystals. Melting point: 267-268° C. (decomposed).

PREPARATION EXAMPLE 13 Preparation of 3-(4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 1)

7.0 g (17 mmol) of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 5.0 g (79 mmol) of copper powder, were suspended in 50 ml of quinoline, followed by stirring at 200° C. for 1 hour. After completion of the reaction, the reaction solution was subjected to filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution and water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography, to obtain 3.5 g (yield: 56%) of the desired product as white crystals. Melting point: 127-128° C.

PREPARATION EXAMPLE 14 Preparation of 3-(4-chloro-2-propionyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 29)

1.3 g (1.4 mmol) of 3-(4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.9 g (1.4 mmol) of aluminum chloride, were dissolved in 20 ml of nitromethane, and 0.5 g (1.4 mmol) of propionyl chloride was dropwise added thereto under cooling with ice. After completion of the dropwise addition, the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated s odium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.33 g (yield: 56%) of the desired product as a yellow glassy substance. Refractive index: unmeasurable, ¹ H-NMR (solvent, CDCl₃): 1.20(3H,m), 2.91(2H,q), 3.56(3H,s), 6.38(1H,s), 7.28(1H,d), 7.58(1H,s)ppm

PREPARATION EXAMPLE 15 Preparation of 3-[4-chloro-6-fluoro-2-(1-methoxyiminoethyl) benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 37)

20 ml of methanol was added to 0.4 g (1 mmol) of 3-(2-acetyl-4-chloro-6-fluorobenzofuran-7-yl) -1-methyl-6-trifluoromethyluracil, 0.4 g (4 mmol) of potassium acetate and 0.33 g (4 mmol) of methoxyamine hydrochloride, followed by stirring at room temperature for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified directly by silica gel column chromatography to obtain 0.28 g (yield: 64.6%) of the desired product as white powder. Melting point: 176-178° C.

PREPARATION EXAMPLE 16 Preparation of 3-(4-chloro-2-methylhydrazonomethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 231)

0.4 g (1.0 mmol) of 3-(4-chloro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 5 ml of tetrahydrofuran, and 0.1 g (21.7 mmol) of monomethylhydrazine was added thereto under cooling with ice, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.2 g (yield: 47.6%) of the desired product as a pale yellow glassy substance. Refractive index: unmeasurable, ¹ H-NMR (solvent, CDCl₃): 2.90(3H,s), 3.52(3H,s), 6.18(1H,bs), 6.40(1H,s), 6.85(1H,s), 7.05 (1H,d), 7.25(1H,s), 7.29(1H,d) ppm

PREPARATION EXAMPLE 17 Preparation of 3-[4-chloro-6-fluoro-2-(1-hydroxyethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 13)

4.0 g (10.2 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 20 ml of tetrahydrofuran, and 12.3 ml of methyl magnesium bromide (1.0M tetrahydrofuran solution) was dropwise added thereto at -65° C. After stirring at room temperature for 1 hour, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.3 g (yield: 55.3%) of the desired product as pale yellow crystals. Melting point: 154-157° C.

PREPARATION EXAMPLE 18 Preparation of 3-(2-acetyl-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 28)

1.5 g (3.7 mmol) of 3-[4-chloro-6-fluoro-2-(1-hydroxyethyl) benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil was dissolved in 20 ml of acetone, and a Jones' reagent was dropwise added thereto at 5° C. until the orange color no longer disappeared. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to quantitatively obtain the desired product as pale orange crystals. Melting point: 193-194° C.

PREPARATION EXAMPLE 19 Preparation of 3-(4-chloro-6-fluoro-2-hydroxymethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 12)

1.5 g (3.8 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 10 ml of tetrahydrofuran, and 4.5 ml of diisobutylaluminum hydride (0.94M hexane solution) was dropwise added thereto in a nitrogen stream at 5° C. After stirring at room temperature for 1 hour, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.4 g (yield: 90.7%) of the desired product as pale yellow crystals. Melting point: 198-199° C.

PREPARATION EXAMPLE 20 Preparation of 3-[4-chloro-2-(1-chloroethyl)-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 393)

0.50 g (1.2 mmol) of 3-[4-chloro-2-(1-hydroxyethyl)-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil and 0.64 g (2.5 mmol) of triphenylphosphine were dissolved in 20 ml of acetonitrile, and 0.60 g (2.5 mmol) of chloranil was added thereto at room temperature. After stirring at room temperature for 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a 5% potassium carbonate aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.50 g (yield: 96.2%) of the desired product as a pale brown glassy substance. Refractive index: 1.5639 (20° C.).

PREPARATION EXAMPLE 21 Preparation of 3-(4-chloro-6-fluoro-2-methoxymethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 14)

1.5 g (3.3 mmol) of 3-(2-bromomethyl-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 30 ml of tetrahydrofuran, and 0.7 g (3.6 mmol) of sodium methoxide (28% methanol solution) was dropwise added thereto under cooling with ice. After stirring at room temperature for 5 minutes, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.75 g (yield: 56.0%) of the desired product as a yellowish brown glassy substance. Refractive index: 1.5389 (20° C.).

PREPARATION EXAMPLE 22 Preparation of 3-(4-chloro-2-ethylthiomethyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 22)

1.5 g (3.3 mmol) of 3-(2-bromomethyl-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.7 g (5.1 mmol) of potassium carbonate were suspended in 20 ml of N,N-dimethylformamide, and 0.21 g (3.4 mmol) of ethylmercaptan was added thereto at room temperature, followed by stirring at room temperature for 1 hour. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 83.4%) of the desired product as a yellowish brown glassy substance. Refractive index: 1.5629 (20° C.).

PREPARATION EXAMPLE 23 Preparation of 3-(4-chloro-6-fluoro-2-methylsulfonylmethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 21)

0.5 g (1.2 mmol) of 3-(4-chloro-6-fluoro-2-methylthiomethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.6 g (3.5 mmol) of metachloroperbenzoic acid were suspended in chloroform, followed by stirring at room temperature for 1 hour. After completion of the reaction, ethyl acetate was added to the reaction solution, and the mixture was washed sequentially with water and a 10% sodium hydrogensulfite aqueous solution. Then, the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.5 g (yield: 92.9%) of the desired product as white crystals. Melting point: 209-211° C.

PREPARATION EXAMPLE 24 Preparation of 3-(4-chloro-6-fluoro-2-methoxycarbonylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 43)

0.21 g (0.5 mmol) of 3-(2-carboxy-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.16 g (1.1 mmol) of potassium carbonate were suspended in 10 ml of N,N-dimethylformamide, and 0.15 g (1.1 mmol) of methyl iodide was added thereto at room temperature, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.21 g (yield: 96.8%) of the desired product as yellowish brown crystals. Melting point: 194-196° C.

PREPARATION EXAMPLE 25 Preparation of 3-(4-chloro-2-ethylcarbamoylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 248)

10 ml of thionyl chloride was added to 0.37 g (0.96 mmol) of 3-(2-carboxy-4-chlorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, followed by stirring for 3 hours under heating and refluxing. After completion of the reaction, thionyl chloride was distilled off under reduced pressure. The obtained residue was dissolved in 20 ml of tetrahydrofuran. To this solution, 0.24 g (3.84 mmol) of ethylamine (70% aqueous solution) was added, followed by stirring for 10 minutes at room temperature. After completion of the reaction, the reaction solution was poured into water, and precipitated crystals were collected by filtration to obtain 0.31 g (yield: 78.3%) of the desired product as white crystals. Melting point: 225-226° C.

PREPARATION EXAMPLE 26 Preparation of 3-(2-acetoxymethyl-4-chlorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 210)

0.4 g (1.1 mmol) of 3-(4-chloro-2-hydroxymethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 0.13 g (1.2 mmol) of triethylamine were dissolved in 20 ml of tetrahydrofuran, and 0.1 g (1.2 mmol) of acetyl chloride was dropwise added thereto under cooling with ice. After completion of the reaction, the reaction solution was poured into water and washed with ethyl acetate. The organic layer was washed sequentially with a 10% hydrochloric acid aqueous solution, water and a saturated sodium chloride aqueous solution, and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.2 g (yield: 45.5%) of the desired product as white solid. Melting point: 135-138° C.

PREPARATION EXAMPLE 27 Preparation of 3-[4-chloro-6-fluoro-2-(1-dimethylaminoethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 572)

0.5 g (1.2 mmol) of 3-[4-chloro-6-fluoro-2-(1-methylaminoethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil and 0.40 g (2.9 mmol) of potassium carbonate were suspended in 50 ml of N,N-dimethylformamide, and 1.0 g (7.0 mmol) of methyl iodide was added thereto, followed by stirring at 60° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.35 g (yield: 68%) of the desired product as a purple glassy substance. Refractive index: 1.5341 (20° C.)

PREPARATION EXAMPLE 28 Preparation of 3-(3-acetyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 101)

1.6 g (4.2 mmol) of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 50 ml of nitromethane, and 5.6 g (42 mmol) of aluminum chloride was added thereto at room temperature. Further, 3.3 g (42 mmol) of acetyl chloride was dropwise added thereto. After completion of the dropwise addition, stirring was carried out for 5 hours under heating and ref refluxing. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 66.7%) of the desired product as pale yellow crystals. Melting point: 138-140° C.

PREPARATION EXAMPLE 29 Preparation of 3-(4-chloro-6-fluoro-3-formyl-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 91)

2.0 g (53 mmol) of 3-(4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 36.5 g (0.32 mol) of dichloromethyl methyl ether were dissolved in 100 ml of dichloromethane, and 200 ml (0.20 mol) of tin tetrachloride (1M dichloromethane solution) was dropwise added thereto at 0° C. After completion of the dropwise addition, stirring was carried out at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into a mixture of dilute hydrochloric acid and ice and extracted with dichloromethane. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 19.5 g (yield: 90.7%) of the desired product as white crystals. Melting point: 148-150° C.

PREPARATION EXAMPLE 30 Preparation of 3-[4-chloro-6-fluoro-3-(1-methoxyiminoethyl)-2-methylbenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 111)

50 ml of methanol was added to 0.4 g (1 mmol) of 3-(3-acetyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, 0.5 g (5 mmol) of potassium acetate and 0.5 g (6 mmol) of methoxyamine hydrochloride, followed by stirring at room temperature for 12 hours and further for 8 hours under heating and refluxing. After completion of the reaction, methanol was distilled off under reduced pressure, ethyl acetate was added to the obtained residue, and the mixture was washed sequentially with water and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.4 g (yield: 100%) of the desired product as pale yellow crystals. Melting point: 65-67° C., ¹ H-NMR (solvent: CDCl₃): 1.54 (1H,s), 2.21(3H,s), 2.35(3H,s), 3.59(3H,s), 3.91(3H,s), 6.41(1H,s), 7.16(1H,d)ppm

PREPARATION EXAMPLE 31 Preparation of 3-(4-chloro-6-fluoro-2-methyl-3-thioacetylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 631)

100 ml of toluene was added to 0.50 g (1.2 mmol) of 3-(3-acetyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.5 g (6.7 mmol) of phosphorus pentasulfide, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, 100 ml of toluene was further added to the reaction solution. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 47 mg (yield: 9%) of the desired product as an orange colored glassy substance. Refractive index: 1.5967 (20° C.).

PREPARATION EXAMPLE 32 Preparation of 3-(3-bromo-4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 272)

1.0 g (2.8 mmol) of 3-(4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 30 ml of acetic acid, and 0.9 g (5.6 mmol) of bromine was dropwise added thereto at room temperature. After completion of the dropwise addition, stirring was carried out at 40° C. for 6 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and 10% aqueous ammonia and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.6 g (yield: 50.0%) of a pale yellow glassy substance. Refractive index: 1.5632 (20° C.).

PREPARATION EXAMPLE 33 Preparation of 3-(4-chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 303)

0.5 g (1.4 mmol) of 3-(4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 10 ml of concentrated sulfuric acid, and 0.1 g (1.1 mmol) of 60% nitric acid was dropwise added thereto at -20° C. After stirring at -20° C. for 10 minutes, the reaction solution was poured into ice water and extracted with 50 ml of chloroform. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.3 g (yield: 53.3%) of the desired product as a pale yellow crystals. Melting point: 174-175° C.

PREPARATION EXAMPLE 34 Preparation of 3-[4-chloro-2-(1-cyanoethyl)-3-ethoxycarbonyl-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 671)

20 ml of N,N-dimethylformamide was added to 0.8 g (1.6 mmol) of 3-[4-chloro-2-(1-chloroethyl)-3-ethoxycarbonyl-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil, 0.16 g (2.5 mmol) of potassium cyanide and 0.40 g (2.9 mmol) of potassium carbonate, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.58 g (yield: 74%) of the desired product as a yellow glassy substance. Refractive index: 1.5348 (20° C.).

PREPARATION EXAMPLE 35 Preparation of 3-(3-carbamoylmethyl-4-chloro-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 619)

0.50 g (1.2 mmol) of 3-(4-chloro-3-cyanomethyl-6-fluoro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 30 ml of 50% sulfuric acid, followed by stirring at 60° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.39 g (yield: 75%) of the desired product as white crystals. Melting point: 127-129° C.

PREPARATION EXAMPLE 36 Preparation of 3-[4-chloro-6-fluoro-2-(1-thiocyanate ethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 577)

30 ml of ethanol was added to 2.3 g (4.9 mmol) of 3-[2-(1-bromoethyl)-4-chloro-6-fluorobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.5 g (2.3 mmol) of potassium thiocyanate, followed by stirring at 60° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, obtained residue was purified by silica gel column chromatography to obtain 1.1 g (yield: 50%) of the desired product as yellow crystals. Melting point: 60-63° C., ¹ H-NMR (solvent: CDCl₃): 1.93(3H,d), 3.59(3H,s), 4.56(1H,q), 6.40(1H,d), 6.87(1H,s), 7.25(1H,s)ppm

PREPARATION EXAMPLE 37 Preparation of 3-(4-chloro-6-fluoro-2-vinylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 412)

50 ml of dioxane and 0.5 ml of water were added to 1.0 g (2.6 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, 0.94 g (2.6 mmol) of methyltriphenylphosphonium bromide and 0.43 g (3.1 mmol) of potassium carbonate, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, the reaction solution was poured into water and adjusted to pH 3 with an aqueous citric acid solution and then, extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.51 g (yield: 51%) of the desired product as yellow crystals. Melting point: 108-109° C.

PREPARATION EXAMPLE 38

Preparation of 3-[4-chloro-2-(2-oxiranyl)-6-fluorobenzofuran-7-yl]-1-methyl-6-trifluoromethyluracil (Compound No. 606)

50 ml of chloroform was added to 0.4 g (1.0 mmol) of 3-(4-chloro-6-fluoro-2-vinylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil, and 10 ml of a chloroform solution containing 0.21 g (1.0 mmol) of 80% metachloroperbenzoic acid, was dropwise added thereto at room temperature. After stirring at room temperature for 12 hours, the reaction solution was poured into water and extracted with chloroform. The organic layer was washed sequentially with water, a 10% sodium hydrogensulfite aqueous solution and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 85 mg (yield: 21%) of the desired product as white crystals. Melting point: 109-111° C.

PREPARATION EXAMPLE 39 Preparation of 3-(4-chloro-6-fluoro-3-methoxy-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 427)

0.50 g (1.3 mmol) of 3-(4-chloro-6-fluoro-3-hdyroxy-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 2.0 g (1.3 mmol) of cesium fluoride were suspended in 10 ml of N,N-dimethylformamide, and 0.3 g (2.1 mmol) of methyl iodide was added thereto, followed by stirring at 70° C. for 1 hour. After completion of the reaction, ethyl acetate was added to the reaction solution. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.19 g (yield: 35%) of the desired product as white crystals. Melting point: 57-60° C.

PREPARATION EXAMPLE 40 Preparation of 3-(4-chloro-3-hydroxyamino-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil (Compound No. 305)

5 ml of acetic acid, 200 ml of ethyl acetate and 100 ml of water were added to 2.3 g (5.7 mmol) of 3-(4-chloro-2-methyl-3-nitrobenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil and 1.6 g (28 mmol) of iron powder, followed by stirring for 2 hours under heating and refluxing. After completion of the reaction, insoluble matters were filtered off. The organic layer was washed sequentially with water and a sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.2 g (yield: 54%) of the desired product as pale yellow crystals. Melting point: 134-136° C.

REFERENCE EXAMPLE 1 Preparation of 3-(4-chloro-2-fluoro-6-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil

5.7 g (16 mmol) of 3-(4-chloro-2-fluoro-6-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 100 ml of dichloromethane, and 27 ml (80 mmol) of boron tribromide (3.0M dichloromethane solution) was dropwise added at 0° C. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water and neutralized with sodium hydrogencarbonate. It was extracted with dichloromethane. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 5.4 g (yield: 98.2%) of the desired product as white crystals. Melting point: 143-144° C.

REFERENCE EXAMPLE 2 Preparation of 3-(4-chloro-2-fluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluraci

5.4 g (16 mmol) of 3-(4-chloro-2-fluoro-6-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil and 3.3 g (24 mmol) of potassium carbonate were suspended in 50 ml of N,N-dimethylformamide, and 2.7 g (22 mmol) of propargyl bromide was dropwise added at room temperature. After stirring at from 60 to 70° C. for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 5.2 g (yield: 86.7%) of the desired product as white crystals. Melting point: 150-152° C.

REFERENCE EXAMPLE 3 Preparation of 3-(4-chloro-2-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil

41.0 g (122.5 mmol) of 3-(4-chloro-2-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 1000 ml of dichloromethane, and 470 ml (470.8 mmol) of boron tribromide (1.0M dichloromethane solution) was dropwise added at from -10° C. to -5° C. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water and neutralized with sodium hydrogencarbonate. It was extracted with dichloromethane. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 27.6 g (yield: 70.3%) of the desired product as white crystals. Melting point: 198-202° C.

REFERENCE EXAMPLE 4 Preparation of 3-(4-chloro-2-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil

22.6 g (70.5 mmol) of 3-(4-chloro-2-hydroxyphenyl-1-methyl-6-trifluoromethyluracil and 14.5 g (105.1 mmol) of potassium carbonate were suspended in 150 ml of N,N-dimethylformamide, and 11.2 g (94.1 mmol) of propargyl bromide was dropwise added thereto at room temperature. After stirring at 70° C. for 2 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 22.5 g (yield: 89.0%) of the desired product as pale brown powder. Melting point: 147-148° C.

REFERENCE EXAMPLE 5 Preparation of 3-(2,4-difluoro-6-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil

13.6 g (40 mmol) of 3-(2,4-difluoro-6-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 150 ml of dichloromethane, and 66.7 ml (200 mmol) of boron tribromide (3.0M dichloromethane solution) was dropwise added thereto at 0° C. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water and neutralized with sodium hydrogencarbonate. It was extracted with dichloromethane. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 9.8 g (yield: 75.4%) of the desired product as white crystals. Melting point: 195-196° C.

REFERENCE EXAMPLE 6 Preparation of 3-(2,4-difluoro-6-propargyloxyphenyl)-1-methyl-6-trifluoromethyluracil

4.8 g (15 mmol) of 3-(2,4-difluoro-6-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil and 3.2 g (23 mmol) of potassium carbonate were suspended in 50 ml of N,N-dimethylformamide, and 2.5 g (21 mmol) of propargyl bromide was dropwise added thereto at room temperature. After stirring at from 60 to 70° C. for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 5.0 g (yield: 92.63%) of the desired product as yellowish brown powder. Melting point: 159-162° C.

REFERENCE EXAMPLE 7 Preparation of 3-[4-chloro-2-(1-methyl-2-propynyloxy) phenyl]-1-methyl-6-trifluoromethyluracil

1.7 g (5.3 mmol) of 3-(4-chloro-2-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil, 0.63 g (9.0 mmol) of 1-butyn-3-ol and 1.57 g (6.0 mmol) of triphenylphosphine were dissolved in 100 ml of tetrahydrofuran, and 1.0 g (6.0 mmol) of diethyl azodicarboxylate was dropwise added thereto under cooling with ice. After stirring at room temperature for 1 hour, the solvent was distilled off. Then, the obtained residue was purified by silica gel column chromatography to obtain 1.86 g (yield: 93.9%) of the desired product as white crystals. Melting point: 96-99° C.

Now, with respect of some of the compounds of the present invention, ¹ H-NMR data will be shown below.

                  TABLE 25                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                          10   3.61(3H, bs) 6.42(1H, s) 7.26(1H, d)                                      20   2.11(3H, s) 3.59(3H, s) 3.73(2H, s) 6.40(1H, s) 6.70(1H, s)                    7.19(1H, d)                                                               29   1.20(3H, m) 2.91(2H, q) 3.56(3H, s) 6.38(1H, s) 7.28(1H, d)                    7.58(1H, s)                                                               30   1.01(3H, t) 1.78(2H, m) 2.87(2H, t) 3.59(3H, s) 6.41(1H, s)                    7.36(1H, d) 7.57(1H, s)                                                   35   3.60(3H, s) 4.02(3H, s) 6.42(1H, s) 7.07(1H, s) 7.24(1H, d)                    8.00(1H, s)                                                               45   1.37(6H, d) 3.57(3H, s) 5.26(1H, m) 6.39(1H, s) 7.29(1H, d)                    7.56(1H, s)                                                               79   2.29(1H, bs) 2.40(3H, s) 3.57(3H, s) 4.78(1H, s) 6.38(1H, s)                   7.17(1H, d)                                                               80   2.05(3H, s) 2.43(3H, s) 3.57(3H, s) 5.27(2H, s) 6.35(1H, s)                    7.15(1H, d)                                                               86   2.69(3H, s) 3.60(3H, s) 6.43(1H, s) 7.29(1H, d) 8.00(1H, bs)              89   1.38(6H, d) 2.58(3H, s) 3.55(3H, s) 5.26(1H, m) 6.35(1H, s)                    7.20(1H, d)                                                              111   1.54(1H, s) 2.21(3H, s) 2.35(3H, s) 3.59(3H, s) 3.91(3H, s)                    6.41(1H, s) 7.16(1H, d)                                                  119   2.73(3H, s) 3.57(3H, s) 6.37(1H, s) 7.32(1H, d)                          141   1.30(3H, s) 3.16(2H, q) 3.61(3H, s) 6.42(1H, s) 7.31(1H, d)                    10.73(1H, s)                                                             207   1.60(3H, d) 2.59(1H, m) 3.57(3H, s) 4.97(1H, m) 6.40(1H, s)                    6.78(1H, s) 7.09(1H, d) 7.32(1H, d)                                      ______________________________________                                    

                  TABLE 26                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                         231   2.90(3H, s) 3.52(3H, s) 6.18(1H, bs) 6.40(1H, s) 6.85(1H, s)                   7.05(1H, d) 7.25(1H, s) 7.29(1H, d)                                      247   3.17(6H, dd) 3.57(3H, s) 6.39(1H, s) 7.25(1H, d) 7.39(1H, d)             270   2.33(3H, s) 3.60(3H, bs) 6.40(1H, s) 7.0˜7.5(7H, m)                334   1.23(6H, d) 3.43(1H, m) 3.57(3H, s) 6.37(1H, s) 7.18(1H, d)              376   2.67(3H, s) 3.60(3H, s) 6.36(1H, s) 7.21(1H, d) 7.38(1H, d)              401   0.97(3H, m) 1.92(2H, m) 2.34(1H, m) 3.57(3H, s) 4.66(1H, m)                    6.37(1H, s) 6.72(1H, s) 7.19(1H, d)                                      446   0.99(3H, t) 1.20(3H, d) 1.68(2H, m) 2.67(2H, t) 3.31(1H, m)                    3.60(3H, s) 6.41(1H, s) 7.22(1H, d)                                      460   1.16(3H, t) 1.30(3H, t) 2.89(2H, q) 3.29(2H, q) 3.61(3H, s)                    6.42(1H, s) 7.24(1H, d)                                                  463   0.88(3H, m) 1.24(3H, t) 1.93(2H, m) 2.57, 2.73(1H, d)                          2.81(2H, m) 3.52, 3.55(3H, s) 4.67(1H, m) 6.30, 6.36(1H, s)                    7.15(1H, d)                                                              464   0.94(3H, t) 1.27(3H, t) 1.0˜2.0(4H, m) 2.17(1H, m)                       2.86(2H, m) 3.54, 3.57(3H, s) 4.79(1H, m) 6.35, 6.38(1H, s)                    7.15(1H, d)                                                              471   1.33(3H, t) 1.74˜1.78(3H, m) 2.48˜2.74(2H, m)                      3.60(3H, s) 3.99˜4.13(1H, m) 6.40(1H, d) 6.82(1H, s)                     7.24(1H, dd)                                                             472   1.30(3H, t) 1.80(3H, d) 3.0(2H, m) 3.55(3H, s) 4.40(1H, q)                     6.45(1H, d) 7.00(1H, s) 7.24(1H, d)                                      ______________________________________                                    

                  TABLE 27                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                         475   1.03(3H, t) 1.86(5H, m) 2.87(2H, m) 3.60(3H, m) 4.36(1H, q)                    6.39(1H, d) 7.00(1H, s) 7.27(1H, d)                                      483   1.10(3H, t) 2.20(1H, m) 2.50(1H, m) 2.80(3H, s) 3.60(3H, s)                    4.20(1H, m) 6.45(1H, d) 7.05(1H, s) 7.20(1H, d)                          484   1.10(3H, t) 2.20(1H, m) 2.50(1H, m) 2.70(3H, s) 3.60(3H, s)                    4.10(1H, m) 6.20(1H, d) 7.0(1H, s) 7.20(1H, d)                           485   1.09(3H, m) 1.19(3H, t) 1.96(2H, m) 2.45(2H, m) 3.58(3H, s)                    3.82(1H, t) 6.40(1H, d) 6.68(1H, d) 7.17(1H, d)                          486   1.05(3H, t) 1.30(3H, t) 2.56(4H, m) 3.59(3H, s) 3.81(1H, m)                    6.46(1H, d) 6.82(1H, d) 7.22(1H, d)                                      505   1.15(6H, m) 1.28(3H, m) 2.81(3H, m) 3.59(3H, s) 4.16(1H, m)                    6.40(1H, d) 7.09(1H, d) 7.26(1H, d)                                      510   0.86(3H, t) 1.71(3H, s) 2.10(1H, m) 2.35(1H, m) 2.66(3H, d)                    3.51(3H, s) 6.31(1H, s) 6.92(1H, s) 7.18(1H, d)                          511   0.97(3H, t) 1.17(1H, m) 1.43(1H, m) 1.80(3H, s) 2.09(1H, m)                    2.32(1H, m) 2.73(3H, d) 3.59(3H, s) 6.39(1H, d) 6.97(1H, s)                    7.24(1H, d)                                                              515   1.80(3H, d) 3.60(3H, s) 4.60(1H, m) 6.40(1H, s) 6.80(1H, s)                    7.20(1H, d)                                                              549   1.59(6H, s) 2.91(1H, bs) 3.55(3H, s) 6.33(1H, s) 6.65(1H, s)                   7.17(1H, d)                                                              551   1.42(3H, d) 3.58(3H, s) 5.35(1H, m) 6.39, 6.43(1H, s)                          6.75(1H, s) 6.80(1H, bs) 7.25(1H, d)                                     ______________________________________                                    

                  TABLE 28                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                         571   1.45(3H, d) 2.40(3H, s) 3.10(1H, s) 3.60(3H, s) 3.90(1H, q)                    6.40(1H, s) 6.70(1H, s) 7.15(1H, d)                                      577   1.93(3H, d) 3.59(3H, s) 4.56(1H, q) 6.40(1H, d) 6.87(1H, s)                    7.25(1H, s)                                                              585   0.90(3H, t) 1.54(3H, d) 3.45(2H, m) 3.58(3H, s) 4.52(1H, m)                    6.38(1H, d) 6.73(1H, s) 7.20(1H, d)                                      586   0.88(3H, t) 1.5˜1.6(6H, m) 3.38(2H, m) 3.56(3H, s)                       4.55(1H, m) 6.39(1H, d) 6.73(1H, s) 7.18(1H, d)                          623   2.44(3H, s) 3.58(3H, s) 3.80(3H, s) 4.64(2H, s) 6.40(1H, s)                    7.15(1H, d)                                                              624   1.62(3H, d) 2.41(3H, s) 3.59(3H, s) 3.75(3H, s) 4.73(1H, q)                    6.40(1H, s) 7.15(1H, d)                                                  635   2.44(3H, s) 3.54(3H, s) 5.32˜5.50(2H, dd) 6.36(1H, s)                    7.00˜7.15(2H, m)                                                   646   0.96(6H, d) 2.14(1H, m) 3.03(2H, m) 3.59(3H, s) 6.41(1H, s)                    7.31(1H, d) 10.7(1H, s)                                                  647   0.94(6H, d) 2.07(1H, m) 2.84(2H, d) 3.59(3H, s) 3.93(3H, s)                    6.40(1H, s) 7.25(1H, d)                                                  649   0.91(3H, m) 1.33˜1.38(4H, m) 1.66˜1.73(2H, m) 3.12(2H,             m)                                                                             3.60(1H, s) 6.41(1H, s) 7.30(1H, d)                                      655   3.59(3H, s) 3.92(3H, s) 6.40(1H, s) 7.31(1H, d)                                8.20(1H, s)                                                              656   2.56(3H, s) 3.56(3H, s) 4.03(3H, s) 6.41(1H, s)                                7.32(1H, d)                                                              ______________________________________                                    

                  TABLE 29                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                         657   1.56(3H, d) 3.57(4H, m) 3.96(3H, s) 5.18(1H, m) 6.37(1H, d)                    7.28(1H, d)                                                              661   1.44(3H, t) 2.96(3H, s) 3.58(3H, s) 4.46(2H, q) 4.73(2H, s)                    6.39(1H, s) 7.34(1H, d)                                                  664   1.37(3H, t) 1.43(3H, t) 3.08(2H, q) 3.58(3H, s) 4.45(2H, q)                    4.71(2H, s) 6.39(1H, s) 7.34(1H, d)                                      666   1.46(3H, t) 3.58(3H, s) 4.53(2H, q) 6.40(1H, s) 7.39(1H, d)                    10.04(1H, s)                                                             670   1.43(3H, t) 1.88(3H, d) 3.60(3H, s) 4.45(2H, q) 5.62(1H, q)                    6.41(1H, s) 7.29(1H, d)                                                  678   1.50(3H, d) 3.30(3H, d) 3.60(3H, s) 4.40(1H, m) 6.40(1H, d)                    6.80(1H, s) 6.90(1H, dd)                                                 684   1.8(3H, dd) 2.75(3H, s) 3.80(3H, s) 4.20(1H, q) 6.20(1H, d)                    7.00(2H, m)                                                              688   1.38(3H, t) 1.80(3H, dd) 2.90(2H, m) 3.60(3H, d) 4.40(1H, q)                   6.40(1H, d) 7.00(2H, m) 7.20(1H, s)                                      691   0.89(3H, m) 1.84(2H, m) 3.27(3H, s) 3.53(3H, s) 4.13(1H, q)                    6.35(1H, d) 6.72(1H, d) 6.87(1H, dd)                                     694   1.04(3H, t) 1.31(3H, t) 2.17(1H, m) 2.45(1H, m) 2.87(2H, m)                    3.58(3H, s) 4.19(1H, m) 6.39(1H, d) 6.96(1H, dd) 7.03(1H, d)             712   1.00(2H, t) 1.90(2H, m) 2.60(1H, bs) 3.50(3H, s) 3.60(1H, q)                   6.30(1H, s) 6.60(1H, s) 7.40(1H, d)                                      ______________________________________                                    

                  TABLE 30                                                         ______________________________________                                         Comp.                                                                          Nos.  .sup.1 H-NMR δ value (ppm) Solvent CDCl.sub.3                      ______________________________________                                         713   1.53(3H, d) 3.31(3H, d) 3.58(3H, s) 4.45(1H, m) 6.39(1H, d)                    6.70(1H, s) 7.35(1H, d)                                                  717   1.82(3H, dd) 2.82(3H, s) 3.57(3H, s) 4.37(1H, q) 6.39(1H, d)                   6.96(1H, s) 7.41(1H, d)                                                  720   1.35(3H, m) 1.83(3H, dd) 2.92(2H, m) 3.59(3H, s) 4.39(1H, q)                   6.39(1H, d) 6.95(1H, s) 7.40(1H, d)                                      750   1.33(3H, t) 2.80(2H, q) 3.70(3H, s) 6.35(1H, s) 6.47(1H, s)                    7.23(1H, d)                                                              752   1.63(3H, d) 3.07(2H, m) 3.56(3H, d) 4.27(1H, q) 6.37(1H, d)                    6.71(1H, d) 7.19(1H, d)                                                  757   1.11(3H, m) 2.20(1H, m) 2.54(1H, m) 3.53˜3.62(4H, m)                     3.86(1H, m) 4.36(1H, m) 6.38(1H, d) 7.05(1H, s) 6.26(1H, d)              764   0.85(3H, m) 1.82(2H, m) 3.24(3H, s) 3.51(3H, s) 4.11(1H, q)                    6.32(1H, d) 6.98(1H, d) 7.12(1H, d)                                      765   1.61(3H, d) 3.73(3H, s) 3.79(2H, m) 4.73(1H, m) 6.38(1H, s)                    6.81(1H, s) 7.23(1H, d)                                                  766   1.54(3H, d) 3.58(3H, s) 3.71(2H, m) 4.45(1H, m) 4.64(2H, m)                    6.39(1H, s) 6.78(1H, s) 7.19(1H, d)                                      770   1.22˜1.28(6H, m) 1.79(3H, dd) 3.59(3H, s) 3.66˜4.07(4H,            dd)                                                                            5.47(1H, m) 6.39(1H, d) 6.79(1H, s) 7.16(1H, d)                          771   0.93(3H, m) 1.84(2H, m) 3.31(3H, s) 3.57(3H, s) 4.17(1H, q)                    6.38(1H, q) 6.75(1H, d) 6.90(1H, dd)                                     ______________________________________                                    

The herbicide of the present invention comprises a benzofuran-7-yl uracil derivative of the formula (1) as an active ingredient.

For the compound of the present invention to be used as a herbicide, the compound of the present invention may be used by itself. However, it may be used in the form of a formulation such as a dust, a wettable powder, an emulsifiable concentrate, a microgranule or a granule by blending it with a carrier, a surfactant, a dispersant or an adjuvant, which is commonly used for formulations.

The carrier to be used for such formulations, may, for example, be a solid carrier such as talc, bentonite, clay, kaolin, diatomaceous earth, fine silica, vermiculite, calcium carbonate, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexane or methylnaphthalene.

As the surfactant and dispersant, a metal salt of alkylbenzenesulfonic acid, a metal salt of dinaphthylmethane disulfonic acid, a salt of alcohol sulfuric acid ester, an alkylaryl sulfonate, a lignin sulfonate, a polyoxyethylene glycol ether, a polyoxyethylene alkylaryl ether or a polyoxyethylene sorbitol monoalkylate may, for example, be mentioned. The adjuvant may, for example, be carboxymethyl cellulose, polyethylene glycol or gum arabic. In practical use, the herbicide may be diluted to a suitable concentration before application, or may be directly applied.

The herbicide of the present invention may be used for application to foliage, soil or water surface. The blending proportion of the active ingredient is suitably selected as the case requires. However, in a case of a dust or a granule, the proportion of the active ingredient is selected suitably within a range of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. In a case of an emulsifiable concentrate or a wettable powder, the proportion is selected suitably within a range of from 1 to 50% by weight, preferably from 5 to 30% by weight.

The dose of the herbicide of the present invention varies depending upon the type of the compound, the weeds to be controlled, the germination tendency, the environmental conditions and the type of the formulation to be used. However, in the case of a dust or a granule which is used by itself, the dose of the active ingredient is selected suitably within a range of from 0.1 g to 5 kg, preferably from 1 g to 1 kg, per 10 ares. In a case of an emulsifiable concentrate or a wettable powder which is used in a liquid state, the dose of the active ingredient is selected suitably within a range of from 0.1 to 50,000 ppm, preferably from 10 to 10,000 ppm.

Further, the compound of the present invention may be used in combination with an insecticide, a fungicide, other herbicide, a plant growth controlling agent, a fertilizer or the like, as the case requires.

Now, the formulation method will be described with reference to typical Formulation Examples. The compounds, types of the additives and blending ratios are not limited to such specific Examples and may be changed within wide ranges. In the following description, "parts" means "parts by weight".

FORMULATION EXAMPLE 1

(Wettable powder)

To 10 parts of Compound (4), 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth and 69 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 2

(Wettable powder)

To 10 parts of Compound (78), 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of clay were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 3

(Wettable powder)

To 10 parts of Compound (201), 0.5 part of polyoxyethyleneoctylphenyl ether, 0.5 part of sodium β-naphthalene sulfonate-formalin condensate, 20 parts of diatomaceous earth, 5 parts of fine silica and 64 parts of calcium carbonate, were mixed and pulverized to obtain a wettable powder.

FORMULATION EXAMPLE 4

(Emulsifiable concentrate)

To 30 parts of Compound (8), 60 parts of a mixture comprising equal amounts of xylene and isophorone and 10 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate, were added, and the mixture was thoroughly stirred to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 5

(Granule)

10 Parts of Compound (44), 80 parts of a bulking agent comprising a 1:3 mixture of talc and bentonite, 5 parts of fine silica, 5 parts of a mixture comprising a polyoxyethylene sorbitol alkylate surfactant, a polyoxyethylenealkylaryl polymer and an alkylaryl sulfonate and 10 parts of water were mixed and thoroughly kneaded to obtain a paste, which was extruded from sieve apertures with a diameter of 0.7 mm. The extruded product was dried and then cut into a length of from 0.5 to 1 mm to obtain granules.

Now, the effects of the compounds of the present invention will be described with reference to Test Examples. Further, as comparative agents, the following compounds were used. ##STR92##

Test Example 1

(Test on herbicidal effects by paddy field soil treatment)

In a plastic pot (surface area: 100 cm²) filled with paddy field soil, barnyardgrass (Ec), monochoria (Mo) and bulrush (Sc) were sown after puddling and leveling, and flooded to a water depth of 3 cm. Next day, a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied dropwise to the water surface. The dose was 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 32-40.

                  TABLE 31                                                         ______________________________________                                                       Herbicidal effects                                               Index         (growth-controlling degree)                                      No.           or phytotoxicity                                                 ______________________________________                                         5             Herbicidal effect or phytotoxicity:                                            at least 90%                                                     4             Herbicidal effect or phytotoxicity:                                            at least 70% and less than 90%                                   3             Herbicidal effect or phytotoxicity:                                            at least 50% and less than 70%                                   2             Herbicidal effect or phytotoxicity:                                            at least 30% and less than 50%                                   1             Herbicidal effect or phytotoxicity:                                            at least 10% and less than 30%                                   0             Herbicidal effect or phytotoxicity:                                            0 to less than 10%                                               ______________________________________                                    

                  TABLE 32                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         1          5             5     5                                               2          5             5     5                                               3          5             5     5                                               4          5             5     5                                               6          5             5     5                                               7          5             5     5                                               8          5             5     5                                               9          5             5     5                                               10         5             5     5                                               12         5             5     5                                               13         5             5     5                                               14         5             5     5                                               15         5             5     5                                               16         5             5     5                                               19         5             5     5                                               20         5             5     5                                               21         5             5     5                                               22         5             5     5                                               23         5             5     5                                               28         5             5     5                                               29         5             5     5                                               30         5             5     5                                               31         5             5     5                                               33         5             5     5                                               35         5             5     5                                               37         5             5     5                                               42         5             5     5                                               43         5             5     5                                               44         5             5     5                                               ______________________________________                                    

                  TABLE 33                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         45         5             5     5                                               70         5             5     5                                               71         5             5     5                                               72         5             5     5                                               75         5             5     5                                               78         5             5     5                                               83         5             5     5                                               84         5             5     5                                               95         5             5     5                                               98         5             5     5                                               101        5             5     5                                               111        5             5     5                                               140        5             5     5                                               141        5             5     5                                               142        5             5     5                                               143        5             5     5                                               147        5             5     5                                               152        5             5     5                                               153        5             5     5                                               165        5             5     5                                               166        5             5     5                                               187        5             5     4                                               195        5             5     5                                               196        5             5     5                                               197        5             5     5                                               198        5             5     5                                               200        5             5     5                                               201        5             5     5                                               202        5             5     5                                               ______________________________________                                    

                  TABLE 34                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         207        5             5     5                                               208        5             5     5                                               209        5             5     5                                               210        5             5     5                                               213        5             5     5                                               222        5             5     5                                               228        5             5     5                                               233        5             5     5                                               230        5             5     5                                               239        5             5     5                                               245        5             5     5                                               265        5             5     5                                               266        5             5     5                                               272        5             5     5                                               289        5             5     5                                               299        5             5     5                                               303        5             5     5                                               350        5             5     5                                               374        5             5     5                                               375        5             5     5                                               379        5             5     5                                               383        5             5     5                                               392        5             5     5                                               393        5             5     5                                               394        5             5     5                                               397        5             5     5                                               398        5             5     5                                               400        5             5     5                                               401        5             5     5                                               ______________________________________                                    

                  TABLE 35                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         402        5             5     5                                               404        5             5     5                                               405        5             5     5                                               406        5             5     5                                               407        5             5     5                                               409        5             5     5                                               410        5             5     5                                               411        5             5     5                                               412        5             5     5                                               417        5             5     5                                               418        5             5     5                                               421        5             5     5                                               423        5             5     5                                               424        5             5     5                                               427        5             5     5                                               432        5             5     5                                               433        5             5     5                                               435        5             5     5                                               436        5             5     5                                               439        5             5     5                                               440        5             5     5                                               441        5             5     5                                               442        5             5     5                                               443        5             5     5                                               444        5             5     5                                               445        5             5     5                                               446        5             5     5                                               447        5             5     5                                               448        5             5     5                                               ______________________________________                                    

                  TABLE 36                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         449        5             5     5                                               450        5             5     5                                               451        5             5     5                                               452        5             5     5                                               453        5             5     5                                               454        5             5     5                                               455        5             5     5                                               456        5             5     5                                               457        5             5     5                                               458        5             5     5                                               459        5             5     5                                               460        5             5     5                                               461        5             5     5                                               462        5             5     5                                               463        5             5     5                                               464        5             5     5                                               466        5             5     4                                               467        5             5     5                                               468        5             5     5                                               469        5             5     5                                               470        5             5     5                                               471        5             5     5                                               472        5             5     5                                               473        5             5     5                                               476        5             5     5                                               479        5             5     5                                               482        5             5     5                                               483        5             5     5                                               484        5             5     5                                               ______________________________________                                    

                  TABLE 37                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         508        5             5     5                                               510        5             5     5                                               511        5             5     5                                               513        5             5     5                                               515        5             5     5                                               521        5             5     5                                               524        5             5     5                                               539        5             5     5                                               571        5             5     5                                               572        5             5     5                                               577        5             5     5                                               578        5             5     5                                               584        5             5     5                                               591        5             5     5                                               592        5             5     5                                               605        5             5     5                                               606        5             5     5                                               607        5             5     5                                               610        5             5     5                                               612        5             5     5                                               617        5             5     5                                               618        5             5     5                                               619        5             5     5                                               622        5             5     5                                               623        5             5     5                                               624        5             5     5                                               630        5             5     5                                               631        5             5     5                                               634        5             5     5                                               ______________________________________                                    

                  TABLE 38                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         635        5             5     5                                               636        5             5     5                                               639        5             5     5                                               640        5             5     5                                               641        5             5     5                                               642        5             5     4                                               643        5             5     5                                               644        5             5     5                                               645        5             5     5                                               646        5             5     5                                               647        5             5     5                                               648        5             5     5                                               649        5             5     5                                               650        5             5     5                                               651        5             5     5                                               653        5             5     4                                               655        5             5     5                                               656        5             5     5                                               657        5             5     5                                               658        5             5     5                                               659        5             5     5                                               660        5             5     5                                               661        5             5     5                                               662        5             5     5                                               663        5             5     5                                               664        5             5     5                                               665        5             5     5                                               666        5             5     5                                               667        5             5     5                                               ______________________________________                                    

                  TABLE 39                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         668        5             5     5                                               669        5             5     5                                               670        5             5     5                                               671        5             5     5                                               672        5             5     5                                               674        5             5     5                                               676        5             5     5                                               677        5             5     5                                               680        5             5     5                                               681        5             5     5                                               682        5             5     5                                               684        5             5     5                                               685        5             5     5                                               686        5             5     5                                               688        5             5     5                                               698        5             5     5                                               699        5             5     5                                               700        5             5     5                                               701        5             5     5                                               702        5             5     5                                               703        5             5     5                                               704        5             5     4                                               705        5             5     5                                               706        5             5     5                                               707        5             5     5                                               708        5             5     5                                               709        5             5     5                                               710        5             5     5                                               711        5             5     5                                               ______________________________________                                    

                  TABLE 40                                                         ______________________________________                                         Compound   Herbicidal effects                                                  Nos.       Ec            Mo    Sc                                              ______________________________________                                         712        5             5     5                                               724        5             5     5                                               725        5             5     5                                               726        5             5     5                                               727        5             5     5                                               ______________________________________                                    

Test Example 2

(Test on herbicidal effects by upland field soil treatment)

In a plastic pot (surface area: 120 cm²) filled with sand, pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and covered with soil. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit./10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 41-49. Symbol - represents "not tested".

                  TABLE 41                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         1            5     5           5   5                                           2            5     5           5   5                                           3            5     5           5   5                                           4            5     5           5   5                                           6            5     5           5   5                                           7            5     5           5   5                                           8            5     5           5   5                                           9            5     5           5   5                                           10           5     5           5   5                                           12           5     5           5   5                                           13           5     5           5   5                                           14           5     5           5   5                                           15           5     5           5   5                                           16           5     5           5   5                                           19           5     5           5   5                                           20           5     5           5   5                                           21           5     5           5   5                                           22           5     5           5   5                                           23           5     5           5   5                                           25           5     5           5   5                                           28           5     5           5   5                                           29           5     5           5   5                                           30           5     5           5   5                                           31           5     5           5   5                                           33           5     5           5   5                                           35           5     5           5   5                                           37           5     5           5   5                                           42           5     5           5   5                                           43           5     5           5   5                                           ______________________________________                                    

                  TABLE 42                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         44            5     5           5   5                                          45            5     5           5   5                                          70            5     5           5   5                                          71            5     5           5   5                                          72            5     5           5   5                                          74            5     5           5   5                                          75            5     5           5   5                                          78            5     5           5   5                                          83            5     5           5   5                                          84            5     5           5   5                                          95            5     5           5   5                                          98            5     5           5   5                                          101           5     5           5   5                                          111           5     5           5   5                                          117           5     5           5   5                                          140           5     5           5   5                                          141           5     5           5   5                                          142           5     5           5   5                                          143           5     5           5   5                                          147           5     5           5   5                                          152           5     5           5   5                                          153           5     5           5   5                                          165           5     5           5   5                                          166           5     5           5   5                                          195           5     5           5   5                                          196           5     5           5   5                                          197           5     5           5   5                                          198           5     5           5   5                                          200           5     5           5   5                                          ______________________________________                                    

                  TABLE 43                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         201           5     5           5   5                                          202           5     5           5   5                                          206           5     5           5   5                                          207           5     5           5   5                                          208           5     5           5   5                                          209           5     5           5   5                                          210           5     5           5   5                                          213           5     5           5   5                                          219           5     5           5   5                                          222           5     5           5   5                                          227           5     5           5   5                                          228           5     5           5   5                                          230           5     5           5   5                                          231           5     5           5   5                                          233           5     5           5   5                                          238           5     5           5   5                                          239           5     5           5   5                                          240           5     5           5   5                                          241           5     5           5   5                                          245           5     5           5   5                                          246           5     5           5   5                                          247           5     5           5   5                                          248           5     5           5   5                                          265           5     5           5   5                                          266           5     5           5   5                                          267           5     5           5   5                                          269           5     5           5   5                                          270           5     5           5   5                                          272           5     5           5   5                                          ______________________________________                                    

                  TABLE 44                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         289           5     5           5   5                                          299           5     5           5   5                                          301           5     5           5   5                                          303           5     5           5   5                                          305           5     5           5   5                                          349           5     5           5   5                                          350           5     5           5   5                                          374           5     5           5   5                                          375           5     5           5   5                                          379           5     5           5   5                                          383           5     5           5   5                                          392           5     5           5   5                                          393           5     5           5   5                                          394           5     5           5   5                                          397           5     5           5   5                                          398           5     5           5   5                                          400           5     5           5   5                                          401           5     5           5   5                                          402           5     5           5   5                                          404           5     5           5   5                                          405           5     5           5   5                                          406           5     5           5   5                                          407           5     5           5   5                                          409           5     5           5   5                                          410           5     5           5   5                                          411           5     5           5   5                                          412           5     5           5   5                                          417           5     5           5   5                                          418           5     5           5   5                                          ______________________________________                                    

                  TABLE 45                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         421           5     5           5   5                                          423           5     5           5   5                                          424           5     5           5   5                                          427           5     5           5   5                                          432           5     5           5   5                                          433           5     5           5   5                                          435           5     5           5   5                                          436           5     5           5   5                                          439           5     5           5   --                                         440           5     5           5   5                                          441           5     5           5   --                                         442           5     5           5   5                                          443           5     5           5   5                                          444           5     5           5   5                                          445           5     5           5   5                                          446           5     5           5   5                                          447           5     5           5   5                                          448           5     5           5   5                                          449           5     5           5   5                                          450           5     5           5   5                                          452           5     5           5   --                                         453           5     5           5   5                                          454           5     5           5   5                                          455           5     5           5   5                                          456           5     5           5   5                                          457           5     5           5   5                                          458           5     5           5   5                                          459           5     5           5   5                                          460           5     5           5   5                                          ______________________________________                                    

                  TABLE 46                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         461           5     5           5   5                                          462           5     5           5   5                                          463           5     5           5   5                                          464           5     5           5   5                                          466           5     5           5   5                                          467           5     5           5   5                                          468           5     5           5   5                                          469           5     5           5   5                                          470           5     5           5   --                                         471           5     5           5   5                                          472           5     5           5   --                                         473           5     5           5   5                                          482           5     5           5   5                                          483           5     5           5   5                                          484           5     5           5   5                                          508           5     5           5   5                                          510           5     5           5   5                                          511           5     5           5   5                                          513           5     5           5   5                                          515           5     5           5   5                                          521           5     5           5   5                                          524           5     5           5   5                                          539           5     5           5   5                                          571           5     5           5   5                                          572           5     5           5   5                                          577           5     5           5   5                                          578           5     5           5   5                                          584           5     5           5   5                                          591           5     5           5   5                                          ______________________________________                                    

                  TABLE 47                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         592           5     5           5   5                                          605           5     5           5   5                                          606           5     5           5   5                                          607           5     5           5   5                                          610           5     5           5   5                                          612           5     5           5   5                                          617           5     5           5   5                                          618           5     5           5   5                                          619           5     5           5   5                                          622           5     5           5   5                                          623           5     5           5   5                                          624           5     5           5   5                                          630           5     5           5   5                                          631           5     5           5   5                                          632           5     5           5   5                                          634           5     5           5   5                                          635           5     5           5   5                                          636           5     5           5   5                                          639           5     5           5   5                                          640           5     5           5   5                                          643           5     5           5   5                                          644           4     5           5   5                                          645           5     5           5   5                                          646           5     5           5   5                                          647           5     5           5   5                                          648           5     5           5   5                                          649           5     5           5   5                                          651           5     5           5   5                                          652           5     5           5   5                                          ______________________________________                                    

                  TABLE 48                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         653           5     5           5   5                                          655           5     5           5   5                                          656           5     5           5   5                                          657           5     5           5   5                                          658           5     5           5   5                                          659           5     5           5   --                                         660           5     5           5   5                                          661           5     5           5   5                                          662           5     5           5   5                                          663           5     5           5   5                                          664           5     5           5   5                                          665           5     5           5   5                                          666           5     5           5   5                                          667           5     5           5   5                                          668           5     5           5   5                                          669           5     5           5   5                                          670           5     5           5   5                                          671           5     5           5   5                                          672           5     5           5   5                                          673           5     5           5   5                                          674           5     5           5   5                                          675           5     5           5   5                                          676           5     5           5   5                                          677           5     5           5   5                                          680           5     5           5   5                                          681           5     5           5   5                                          682           5     5           5   5                                          684           5     5           5   5                                          685           5     5           5   5                                          ______________________________________                                    

                  TABLE 49                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         686           5     5           5   5                                          688           5     5           5   5                                          698           5     5           5   --                                         699           5     5           5   --                                         700           5     5           5   --                                         701           5     5           5   5                                          702           5     5           5   --                                         703           5     5           5   --                                         704           5     5           5   --                                         705           5     5           5   5                                          706           5     5           5   5                                          707           5     5           5   5                                          708           5     5           5   5                                          709           5     5           5   5                                          710           5     5           5   5                                          711           5     5           5   5                                          712           5     5           5   5                                          724           5     5           5   5                                          725           5     5           5   5                                          726           5     5           5   5                                          727           5     5           5   5                                          730           5     5           5   5                                          ______________________________________                                    

Test Example 3

(Test on herbicidal effects by upland field foliage treatment)

In a plastic pot (surface area: 120 cm²) filled with sand, pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and rice flatsedge (Ci) were sown and were cultured in a green house for 2 weeks. A wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 lit./10 ares so as to apply 100 g of the active ingredient per 10 ares. The plants were then cultured in the green house, and the evaluation of the herbicidal effects was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Tables 50-58.

                  TABLE 50                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         1             5     5           5   5                                          2             5     5           5   5                                          3             5     5           5   5                                          4             5     5           5   5                                          6             5     5           5   5                                          7             5     5           5   5                                          8             5     5           5   5                                          9             5     5           5   5                                          10            5     5           5   5                                          12            5     5           5   5                                          13            5     5           5   5                                          14            5     5           5   5                                          15            5     5           5   5                                          16            5     5           5   5                                          19            5     5           5   5                                          20            5     5           5   5                                          21            5     5           5   5                                          22            5     5           5   5                                          23            5     5           5   5                                          25            5     5           5   5                                          28            5     5           5   5                                          29            5     5           5   5                                          30            5     5           5   5                                          31            5     5           5   5                                          33            5     5           5   5                                          35            5     5           5   5                                          37            5     5           5   5                                          42            5     5           5   5                                          43            5     5           5   5                                          ______________________________________                                    

                  TABLE 51                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         44            5     5           5   5                                          45            5     5           5   5                                          70            5     5           5   5                                          71            5     5           5   5                                          72            5     5           5   5                                          74            5     5           5   5                                          75            5     5           5   5                                          78            5     5           5   5                                          83            5     5           5   5                                          84            5     5           5   5                                          95            5     5           5   5                                          98            5     5           5   5                                          101           5     5           5   5                                          111           5     5           5   5                                          116           5     5           5   5                                          140           5     5           5   5                                          141           5     5           5   5                                          142           5     5           5   5                                          143           5     5           5   5                                          147           5     5           5   5                                          152           5     5           5   5                                          153           5     5           5   5                                          165           5     5           5   5                                          166           5     5           5   5                                          195           5     5           5   5                                          196           5     5           5   5                                          197           5     5           5   5                                          198           5     5           5   5                                          200           5     5           5   5                                          ______________________________________                                    

                  TABLE 52                                                         ______________________________________                                         Compound      Herbicidal effects                                               Nos.          Po    Am          Ch  Ci                                         ______________________________________                                         201           5     5           5   5                                          202           5     5           5   5                                          206           5     5           5   5                                          207           5     5           5   5                                          208           5     5           5   5                                          209           5     5           5   5                                          210           5     5           5   5                                          213           5     5           5   5                                          219           5     5           5   5                                          222           5     5           5   5                                          227           5     5           5   5                                          228           5     5           5   5                                          230           5     5           5   5                                          231           5     5           5   5                                          233           5     5           5   5                                          238           5     5           5   5                                          239           5     5           5   5                                          240           5     5           5   5                                          241           5     5           5   5                                          245           5     5           5   5                                          246           5     5           5   5                                          247           5     5           5   5                                          248           5     5           5   5                                          265           5     5           5   5                                          266           5     5           5   5                                          267           5     5           5   5                                          269           5     5           5   5                                          272           5     5           5   5                                          289           5     5           5   5                                          ______________________________________                                    

                  TABLE 53                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         299          5     5           5   5                                           301          5     5           5   5                                           303          5     5           5   5                                           305          5     5           5   5                                           349          5     5           5   5                                           350          5     5           5   5                                           374          5     5           5   5                                           375          5     5           5   5                                           379          5     5           5   5                                           383          5     5           5   5                                           392          5     5           5   5                                           393          5     5           5   5                                           394          5     5           5   5                                           397          5     5           5   5                                           398          5     5           5   5                                           400          5     5           5   5                                           401          5     5           5   5                                           402          5     5           5   5                                           404          5     5           5   5                                           405          5     5           5   5                                           406          5     5           5   5                                           407          5     5           5   5                                           409          5     5           5   5                                           410          5     5           5   5                                           411          5     5           5   5                                           412          5     5           5   5                                           417          5     5           5   5                                           418          5     5           5   5                                           421          5     5           5   5                                           ______________________________________                                    

                  TABLE 54                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         423          5     5           5   5                                           424          5     5           5   5                                           427          5     5           5   5                                           432          5     5           5   5                                           433          5     5           5   5                                           435          5     5           5   5                                           436          5     5           5   5                                           439          5     5           5   5                                           440          5     5           5   5                                           441          5     5           5   5                                           442          5     5           5   5                                           443          5     5           5   5                                           444          5     5           5   5                                           445          5     5           5   5                                           446          5     5           5   5                                           447          5     5           5   5                                           448          5     5           5   5                                           449          5     5           5   5                                           450          5     5           5   5                                           451          5     5           5   5                                           452          5     5           5   5                                           453          5     5           5   5                                           454          5     5           5   5                                           455          5     5           5   5                                           456          5     5           5   5                                           457          5     5           5   5                                           458          5     5           5   5                                           459          5     5           5   5                                           460          5     5           5   5                                           ______________________________________                                    

                  TABLE 55                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         461          5     5           5   5                                           462          5     5           5   5                                           463          5     5           5   5                                           464          5     5           5   5                                           466          5     5           5   5                                           467          5     5           5   5                                           468          5     5           5   5                                           469          5     5           5   5                                           470          5     5           5   5                                           471          5     5           5   5                                           472          5     5           5   5                                           473          5     5           5   5                                           476          5     5           5   5                                           479          5     5           5   5                                           482          5     5           5   5                                           483          5     5           5   5                                           484          5     5           5   5                                           508          5     5           5   5                                           510          5     5           5   5                                           511          5     5           5   5                                           513          5     5           5   5                                           515          5     5           5   5                                           521          5     5           5   5                                           524          5     5           5   5                                           539          5     5           5   5                                           571          5     5           5   5                                           572          5     5           5   5                                           577          5     5           5   5                                           578          5     5           5   5                                           ______________________________________                                    

                  TABLE 56                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         584          5     5           5   5                                           591          5     5           5   5                                           592          5     5           5   5                                           605          5     5           5   5                                           606          5     5           5   5                                           607          5     5           5   5                                           610          5     5           5   5                                           612          5     5           5   5                                           617          5     5           5   5                                           618          5     5           5   5                                           619          5     5           5   5                                           622          5     5           5   5                                           623          5     5           5   5                                           624          5     5           5   5                                           630          5     5           5   5                                           631          5     5           5   5                                           632          5     5           5   5                                           634          5     5           5   5                                           635          5     5           5   5                                           636          5     5           5   5                                           639          5     5           5   5                                           640          5     5           5   5                                           641          5     5           5   5                                           643          5     5           5   5                                           644          5     5           5   5                                           645          5     5           5   5                                           646          5     5           5   5                                           647          5     5           5   5                                           648          5     5           5   5                                           ______________________________________                                    

                  TABLE 57                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         649          5     5           5   5                                           651          5     5           5   5                                           653          5     5           5   5                                           655          5     5           5   5                                           656          5     5           5   5                                           657          5     5           5   5                                           658          5     5           5   5                                           659          5     5           5   5                                           660          5     5           5   5                                           661          5     5           5   5                                           662          5     5           5   5                                           663          5     5           5   5                                           664          5     5           5   5                                           665          5     5           5   5                                           666          5     5           5   5                                           667          5     5           5   5                                           668          5     5           5   5                                           669          5     5           5   5                                           670          5     5           5   5                                           671          5     5           5   5                                           672          5     5           5   5                                           674          5     5           5   5                                           676          5     5           5   5                                           677          5     5           5   5                                           680          5     5           5   5                                           681          5     5           5   5                                           682          5     5           5   5                                           684          5     5           5   5                                           685          5     5           5   5                                           ______________________________________                                    

                  TABLE 58                                                         ______________________________________                                         Compound     Herbicidal effects                                                Nos.         Po    Am          Ch  Ci                                          ______________________________________                                         686          5     5           5   5                                           688          5     5           5   5                                           698          5     5           5   5                                           699          5     5           5   5                                           701          5     5           5   5                                           702          5     5           5   5                                           703          5     5           5   5                                           704          5     5           5   5                                           705          5     5           5   5                                           706          5     5           5   5                                           707          5     5           5   5                                           708          5     5           5   5                                           709          5     5           5   5                                           710          5     5           5   5                                           711          5     5           5   5                                           712          5     5           5   5                                           724          5     5           5   5                                           725          5     5           5   5                                           726          5     5           5   5                                           727          5     5           5   5                                           730          5     5           5   5                                           ______________________________________                                    

Test Example 4

(Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, wheat (Tr), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 59-62. Symbol--represents "not tested".

                  TABLE 59                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         3        1.6     5      5     5    5    0                                      6        1.6     5      5     5    5    1                                      8        1.6     5      5     5    5    1                                      13       1.6     5      5     5    5    0                                      15       1.6     5      5     5    5    0                                      22       1.6     5      5     5    5    0                                      23       1.6     5      5     5    5    1                                      31       1.6     5      5     5    5    1                                      33       1.6     5      5     5    5    1                                      70       1.6     5      5     5    5    1                                      71       1.6     5      5     5    5    1                                      72       1.6     5      5     5    5    0                                      78       1.6     5      5     5    5    1                                      84       6.3     5      5     5    5    1                                      95       1.6     5      5     5    5    1                                      98       6.3     5      5     5    5    1                                      111      1.6     5      5     5    5    1                                      142      6.3     5      5     5    5    1                                      152      1.6     5      5     4    5    0                                      153      6.3     5      5     5    5    1                                      165      1.6     5      5     5    5    1                                      200      1.6     5      5     5    5    1                                      222      1.6     5      5     5    5    0                                      233      1.6     5      5     5    5    1                                      245      6.3     5      5     5    5    0                                      246      1.6     5      5     5    5    0                                      247      6.3     5      5     5    5    0                                      266      6.3     5      5     5    5    1                                      289      1.6     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 60                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         374      1.6     5      5     5    5    1                                      379      1.6     5      5     5    5    1                                      383      1.6     5      5     5    5    1                                      392      1.6     5      5     4    5    1                                      394      1.6     5      5     5    5    1                                      397      1.6     5      5     5    5    1                                      398      1.6     5      5     5    4    1                                      402      6.3     5      5     5    5    1                                      406      1.6     5      5     5    5    1                                      407      1.6     5      5     5    5    1                                      409      1.6     5      5     5    5    1                                      410      1.6     5      5     5    5    1                                      411      1.6     5      5     5    5    1                                      417      1.6     5      5     5    5    1                                      421      1.6     5      5     5    5    1                                      423      1.6     5      5     5    5    1                                      432      1.6     5      5     5    5    1                                      435      6.3     5      5     5    5    1                                      436      1.6     5      5     5    5    1                                      439      1.6     5      5     5    5    1                                      440      1.6     5      5     5    5    1                                      441      1.6     5      5     5    5    1                                      444      6.3     5      5     5    5    1                                      447      6.3     5      5     5    5    1                                      448      6.3     5      5     5    5    1                                      454      1.6     5      5     5    5    1                                      458      1.6     5      5     5    5    0                                      459      1.6     5      5     5    5    1                                      462      1.6     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 61                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         467      1.6     5      5     5    5    1                                      468      6.3     5      5     5    5    1                                      471      1.6     5      5     5    5    1                                      482      1.6     5      5     5    --   1                                      515      1.6     5      5     5    5    1                                      524      1.6     5      5     5    5    1                                      539      1.6     5      5     5    5    1                                      578      1.6     5      5     5    5    0                                      617      1.6     5      5     5    5    1                                      619      1.6     5      5     5    5    1                                      630      6.3     4      5     5    5    1                                      639      1.6     5      5     5    5    0                                      648      1.6     5      5     5    5    1                                      656      1.6     5      5     5    5    1                                      658      1.6     5      5     5    5    0                                      661      1.6     5      5     5    5    1                                      662      1.6     5      5     5    5    1                                      665      1.6     5      4     5    4    1                                      667      1.6     5      5     5    5    1                                      668      1.6     5      5     5    5    1                                      669      1.6     5      5     5    5    1                                      672      6.3     5      5     5    5    1                                      677      6.3     5      5     --   5    1                                      682      1.6     5      5     5    5    1                                      699      6.3     5      5     5    4    1                                      702      6.3     5      5     5    5    1                                      705      1.6     5      5     --   5    1                                      708      1.6     5      5     5    5    0                                      724      1.6     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 62                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         Compara- 1.6     5      5     5    5    5                                      tive 1                                                                         Compara- 1.6     5      5     5    5    5                                      tive 2                                                                         ______________________________________                                    

Test Example 5

(Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, soybean (Gl), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 63-64. Symbol--represents "not tested".

                  TABLE 63                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   G1                                     ______________________________________                                         4        1.6     5      5     5    5    1                                      6        1.6     5      5     5    5    1                                      7        1.6     5      5     5    4    0                                      31       1.6     5      5     5    5    1                                      70       1.6     5      5     5    5    0                                      71       1.6     5      5     5    5    1                                      72       1.6     5      5     5    5    0                                      152      1.6     5      5     4    5    1                                      201      6.3     5      5     5    5    0                                      207      1.6     5      5     5    5    1                                      233      6.3     5      5     5    5    1                                      239      6.3     5      5     5    5    1                                      266      6.3     5      5     5    5    0                                      397      1.6     5      5     5    5    1                                      398      1.6     5      5     5    4    1                                      421      1.6     5      5     5    5    1                                      435      6.3     5      5     5    5    1                                      436      1.6     5      5     5    5    1                                      439      1.6     5      5     5    5    1                                      441      1.6     5      5     5    5    1                                      447      6.3     5      5     5    5    1                                      450      6.3     5      5     5    5    1                                      458      1.6     5      5     5    5    0                                      459      1.6     5      5     5    5    1                                      463      6.3     5      5     5    5    1                                      618      1.6     5      5     5    5    0                                      630      6.3     4      5     5    5    1                                      639      1.6     5      5     5    5    1                                      655      6.3     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 64                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   G1                                     ______________________________________                                         656      1.6     5      5     5    5    0                                      658      1.6     5      5     5    5    0                                      661      1.6     5      5     5    5    1                                      662      1.6     5      5     5    5    1                                      665      1.6     5      4     5    4    0                                      667      1.6     5      5     5    5    1                                      668      1.6     5      5     5    5    1                                      669      1.6     5      5     5    5    0                                      680      1.6     5      5     --   4    1                                      702      6.3     5      5     5    5    1                                      707      1.6     5      5     5    5    1                                      708      1.6     5      5     5    5    0                                      724      1.6     5      5     5    5    1                                      Compara- 6.3     5      5     5    5    5                                      tive 1   1.6     5      5     5    5    5                                      Compara- 6.3     5      5     5    5    5                                      tive 2   1.6     5      5     5    5    5                                      ______________________________________                                    

Test Example 6

(Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, corn (Ze), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 65-66. Symbol - represents "not tested".

                  TABLE 65                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Ze                                     ______________________________________                                          3       1.6     5      5     5    5    0                                       6       1.6     5      5     5    5    0                                       7       1.6     5      5     5    4    0                                       43      1.6     5      5     5    5    0                                       70      1.6     5      5     5    5    0                                       72      1.6     5      5     5    5    0                                      152      1.6     5      5     4    5    1                                      239      6.3     5      5     5    5    1                                      246      1.6     5      5     5    5    0                                      266      6.3     5      5     5    5    0                                      374      1.6     5      5     5    5    1                                      397      1.6     5      5     5    5    1                                      406      1.6     5      5     5    5    1                                      432      1.6     5      5     5    5    1                                      441      1.6     5      5     5    5    1                                      454      1.6     5      5     5    5    1                                      458      1.6     5      5     5    5    1                                      515      1.6     5      5     5    5    1                                      524      1.6     5      5     5    5    1                                      618      1.6     5      5     5    5    1                                      630      6.3     4      5     5    5    1                                      658      1.6     5      5     5    5    1                                      661      1.6     5      5     5    5    1                                      665      1.6     5      4     5    4    1                                      699      6.3     5      5     5    4    1                                      705      1.6     5      5                                                               5       1                                                             708      1.6     5      5     5    5    0                                      Compara- 6.3     5      5     5    5    5                                      tive 1   1.6     5      5     5    5    5                                      ______________________________________                                    

                  TABLE 66                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Ze                                     ______________________________________                                         Compara- 6.3     5      5     5    5    5                                      tive 2   1.6     5      5     5    5    5                                      ______________________________________                                    

Test Example 7

(Test on crop plant selectivity by upland field soil treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, cotton (Go), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 21st day after the application in accordance with the standards as identified in Table 31. The results are shown in Tables 67-69. Symbol--represents "not tested".

                  TABLE 67                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Go                                     ______________________________________                                         3        1.6     5      5     5    5    0                                      7        1.6     5      5     5    4    0                                      10       1.6     5      5     5    5    1                                      15       1.6     5      5     5    5    1                                      30       1.6     5      5     5    5    0                                      31       1.6     5      5     5    5    0                                      33       1.6     5      5     5    5    1                                      70       1.6     5      5     5    5    0                                      71       1.6     5      5     5    5    0                                      72       1.6     5      5     5    5    1                                      111      1.6     5      5     5    5    1                                      147      1.6     5      5     5    5    1                                      152      1.6     5      5     4    5    0                                      153      6.3     5      5     5    5    0                                      166      6.3     5      5     5    5    1                                      197      1.6     5      5     5    5    0                                      201      1.6     5      5     5    4    0                                      233      1.6     5      5     5    5    1                                      237      6.3     5      5     5    5    1                                      266      6.3     5      5     5    5    1                                      272      6.3     5      5     5    5    1                                      299      1.6     5      5     5    5    1                                      374      1.6     5      5     5    5    1                                      383      1.6     5      5     5    5    1                                      397      1.6     5      5     5    5    0                                      398      1.6     5      5     5    4    1                                      405      1.6     5      5     5    5    1                                      406      1.6     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 68                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Go                                     ______________________________________                                         410      1.6     5      5     5    5    1                                      411      1.6     5      5     5    5    0                                      417      1.6     5      5     5    5    0                                      418      1.6     5      5     5    5    1                                      421      1.6     5      5     5    5    1                                      424      1.6     5      --    5    5    1                                      432      1.6     5      5     5    5    0                                      435      6.3     5      5     5    5    1                                      436      1.6     5      5     5    5    0                                      442      6.3     5      5     5    5    1                                      444      6.3     5      5     5    5    1                                      448      6.3     5      5     5    5    1                                      454      1.6     5      5     5    5    1                                      458      1.6     5      5     5    5    0                                      459      1.6     5      5     5    5    1                                      463      6.3     5      5     5    5    0                                      468      6.3     5      5     5    5    1                                      471      1.6     5      5     5    5    1                                      515      1.6     5      5     5    5    1                                      571      6.3     4      5     5    5    1                                      577      1.6     5      4     5    5    1                                      578      1.6     5      5     5    5    1                                      618      1.6     5      5     5    5    0                                      630      6.3     4      5     5    5    1                                      631      6.3     5      5     5    5    1                                      639      1.6     5      5     5    5    0                                      655      6.3     5      5     5    5    0                                      656      1.6     5      5     5    5    0                                      658      1.6     5      5     5    5    0                                      ______________________________________                                    

    ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Go                                     ______________________________________                                         661      1.6     5      5     5    5    0                                      665      1.6     5      4     5    4    0                                      666      1.6     5      5     5    5    1                                      667      1.6     5      5     5    5    1                                      668      1.6     5      5     5    5    0                                      669      1.6     5      5     5    5    1                                      672      6.3     5      5     5    5    1                                      680      1.6     5      5     --   4    1                                      699      6.3     5      5     5    4    1                                      702      6.3     5      5     5    5    1                                      705      1.6     5      5     --   5    1                                      706      1.6     5      5     5    5    1                                      707      1.6     5      5     5    5    1                                      708      1.6     5      5     5    5    0                                      724      1.6     5      5     5    5    1                                      Compara- 6.3     5      5     5    5    5                                      tive 1   1.6     5      5     5    5    5                                      Compara- 6.3     5      5     5    5    5                                      tive 2   1.6     5      5     5    5    5                                      ______________________________________                                    

Test Example 8

(Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, rice (Or), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Table 70.

                  TABLE 70                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Or                                     ______________________________________                                          6       1.6     5      5     5    5    1                                       10      1.6     5      5     5    5    1                                       12      0.4     5      5     5    5    1                                       33      1.6     5      5     5    5    1                                       44      0.4     4      5     5    5    0                                       72      1.6     5      5     5    5    1                                       78      0.4     5      5     5    5    1                                      111      0.4     5      5     5    5    1                                      207      0.4     5      5     5    5    1                                      228      1.6     5      5     5    5    1                                      Compara- 1.6     5      5     5    5    5                                      tive 1   0.4     5      5     5    5    3                                      Compara- 1.6     5      5     5    5    5                                      tive 2   0.4     5      5     5    5    4                                      ______________________________________                                    

Test Example 9

(Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, wheat (Tr), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Tables 71-73.

                  TABLE 71                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     10a     Po     Am    Ch   Ab   Tr                                     ______________________________________                                          1       0.4     5      5     5    5    1                                      3        0.4     5      5     5    5    1                                      4        1.6     5      5     5    5    1                                      10       1.6     5      5     5    5    1                                      12       0.4     5      5     5    5    0                                      14       0.4     5      5     5    5    1                                      22       0.4     5      5     5    5    0                                      30       1.6     5      5     5    5    1                                      33       1.6     5      5     5    5    1                                      35       1.6     5      5     5    5    0                                      43       1.6     5      5     5    5    0                                      45       1.6     5      5     5    5    1                                      70       1.6     5      5     5    5    1                                      74       1.6     5      5     5    5    1                                      83       1.6     4      5     5    4    1                                      95       1.6     5      5     5    5    1                                      98       0.4     4      5     5    5    1                                      101      0.4     5      5     5    5    1                                      111      0.4     5      5     5    5    1                                      143      0.4     5      5     5    5    1                                      152      0.4     5      5     5    5    0                                      153      0.4     5      5     5    5    1                                      207      0.4     5      5     5    5    1                                      222      0.4     5      5     5    5    1                                      272      1.6     5      5     5    5    1                                      394      0.4     5      5     5    5    0                                      402      0.4     4      5     5    5    1                                      405      0.4     5      5     5    5    1                                      411      1.6     4      5     5    5    1                                      ______________________________________                                    

                  TABLE 72                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         423      1.6     5      5     5    5    1                                      424      1.6     5      5     5    5    1                                      432      0.4     5      5     5    5    1                                      436      1.6     5      5     5    5    1                                      439      0.4     5      5     4    5    1                                      447      1.6     5      5     4    5    1                                      458      0.4     5      5     5    5    1                                      460      1.6     4      5     4    5    1                                      462      0.4     5      5     5    5    1                                      463      0.4     5      5     5    4    1                                      464      0.4     5      5     5    5    1                                      467      1.6     5      5     5    5    1                                      468      0.4     4      5     5    4    1                                      469      0.4     5      5     5    5    1                                      482      0.4     5      5     5    5    1                                      515      0.4     5      5     4    5    1                                      571      0.4     4      5     5    5    1                                      572      1.6     5      5     5    5    1                                      584      0.4     5      5     5    5    1                                      591      0.4     5      5     5    5    1                                      592      0.4     5      5     5    5    1                                      605      1.6     4      5     5    5    1                                      606      0.4     5      5     4    5    1                                      607      0.4     5      5     4    5    1                                      630      1.6     5      5     5    5    1                                      634      0.4     5      5     5    5    1                                      635      1.6     5      5     5    5    1                                      643      1.6     5      5     5    4    1                                      658      1.6     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 73                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Tr                                     ______________________________________                                         669      1.6     4      5     5    5    1                                      670      1.6     5      5     5    5    1                                      671      1.6     5      5     5    5    1                                      688      0.4     4      5     5    5    1                                      706      1.6     4      5     5    5    1                                      707      0.4     5      5     5    5    0                                      708      0.4     5      5     5    5    1                                      712      0.4     5      5     5    5    1                                      Compara- 1.6     5      5     5    5    5                                      tive     0.4     5      5     5    5    3                                      Compara- 1.6     5      5     5    5    5                                      tive     0.4     5      5     5    5    3                                      ______________________________________                                    

Test Example 10

(Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, corn (Ze), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Tables 74-75.

                  TABLE 74                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Ze                                     ______________________________________                                         4        0.4     5      5     5    4    1                                      6        1.6     5      5     5    5    1                                      7        1.6     5      5     5    5    1                                      22       0.4     5      5     5    5    0                                      70       1.6     5      5     5    5    1                                      72       1.6     5      5     5    5    1                                      74       1.6     5      5     5    5    0                                      78       0.4     5      5     5    5    0                                      83       1.6     4      5     5    4    1                                      95       1.6     5      5     5    5    1                                      101      0.4     5      5     5    5    1                                      111      0.4     5      5     5    5    1                                      140      1.6     5      5     5    5    1                                      142      0.4     5      5     5    5    1                                      152      0.4     5      5     5    5    1                                      195      1.6     4      5     5    5    1                                      207      0.4     5      5     5    5    1                                      222      0.4     5      5     5    5    0                                      228      1.6     5      5     5    5    0                                      265      1.6     5      5     5    5    1                                      272      1.6     5      5     5    5    0                                      394      0.4     5      5     5    5    1                                      411      1.6     4      5     5    5    1                                      423      1.6     5      5     5    5    1                                      435      0.4     5      5     5    5    1                                      463      0.4     5      5     5    4    1                                      464      0.4     5      5     5    5    1                                      468      0.4     4      5     5    4    1                                      482      0.4     5      5     5    5    1                                      ______________________________________                                    

                  TABLE 75                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Ze                                     ______________________________________                                         515      0.4     5      5     4    5    1                                      577      0.4     5      5     4    5    1                                      578      0.4     5      5     5    4    1                                      584      0.4     5      5     5    5    1                                      606      0.4     5      5     4    5    1                                      607      0.4     5      5     4    5    1                                      617      1.6     5      5     5    5    1                                      623      0.4     5      5     5    5    1                                      634      0.4     5      5     5    5    1                                      635      1.6     5      5     5    5    1                                      647      0.4     5      5     5    5    1                                      662      0.4     5      5     5    5    1                                      663      0.4     5      5     5    5    1                                      666      1.6     5      5     5    5    1                                      669      1.6     4      5     5    5    1                                      671      1.6     5      5     5    5    1                                      682      1.6     5      5     5    5    1                                      688      0.4     4      5     5    5    1                                      706      1.6     4      5     5    5    1                                      707      0.4     5      5     5    5    1                                      708      0.4     5      5     5    5    1                                      712      0.4     5      5     5    5    1                                      724      1.6     5      5     5    5    1                                      725      1.6     5      5     5    5    1                                      Compara- 1.6     5      5     5    5    5                                      tive 1   0.4     5      5     5    5    4                                      Compara- 1.6     5      5     5    5    5                                      tive 2   0.4     5      5     5    5    3                                      ______________________________________                                    

Test Example 11

(Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, soybean (Gl), slender amaranth (Am) and velvetleaf (Ab) were sown and cultured in a green house for 2 weeks. Then, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied onto the entire foliages of the plants from above by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 14th day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Table 76.

    ______________________________________                                         Compound  Dose          Herbicidal effects                                                                        Phytotoxicity                               Nos.      ai, g/10a                                                                               Am        Ab    G1                                          ______________________________________                                          7        1.6      5         5     1                                            8        1.6      5         5     1                                            74       1.6      5         5     0                                           463       0.4      5         4     1                                           464       0.4      5         5     1                                           468       0.4      5         4     1                                           635       0.4      5         5     1                                           669       0.4      4         5     1                                           686       0.4      5         5     1                                           701       1.6      5         4     1                                           726       0.4      5         5     1                                           Comparative 1                                                                            1.6      5         5     5                                                     0.4      5         5     5                                           Comparative 2                                                                            1.6      5         5     5                                                     0.4      5         5     5                                           ______________________________________                                    

Test Example 12

(Test on crop plant selectivity by upland field foliage treatment)

In a plastic pot (surface area: 600 cm²) filled with sand, cotton (Go), pale smartweed (Po), slender amaranth (Am), common lambsquarters (Ch) and velvetleaf (Ab) were sown and covered with soil. Next day, a prescribed amount of the active ingredient (g^(ai) /10a) of a wettable powder prepared in accordance with Formulation Example 1 was diluted with water and applied uniformly to the soil surface by a small-sized sprayer in an amount of 100 lit. per 10 ares. The plants were then cultured in a green house, and the evaluation of the herbicidal effects and phytotoxicity was conducted on the 21st day after the treatment in accordance with the standards as identified in Table 31. The results are shown in Table

                  TABLE 77                                                         ______________________________________                                                  Dose                                                                  Compound ai, g   Herbicidal effects                                                                              Phytotoxicity                                Nos.     /10a    Po     Am    Ch   Ab   Go                                     ______________________________________                                         666      1.6     5      5     5    5    1                                      Compara- 1.6     5      5     5    5    5                                      tive 1                                                                         Compara- 1.6     5      5     5    5    5                                      tive 2                                                                         ______________________________________                                     

What is claimed is:
 1. A benzofran-7-yl uracil compound having the formula (1): ##STR93## wherein X is hydrogen or halogen;Y is hydrogen, halogen, cyano, lower alkyl, lower haloalkyl, lower alkoxy or lower haloalkoxy; R¹ is hydrogen, lower alkyl, amino or lower haloalkyl; R² is lower alkyl or lower haloalkyl; R³ is hydrogen, halogen, lower alkyl or lower haloalkyl; R⁵ is hydrogen, lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkenyloxy, lower alkynyloxy, lower alkoxycarbonylalkoxy, lower alkylthio, lower haloalkylthio, lower alkenylthio, lower alkynylthio, lower alkoxycarbonylalkylthio, lower alkylsulfonyl, lower haloalkylsulfonyl, phenylsulfonyl which is optionally substituted by halogen, halogen, hydroxyiminoalkyl, hydroxyiminohaloalkyl, lower alkoxyiminoalkyl, lower alkoxyiminohaloalkyl, lower alkyliminoalkyl, phenyliminoalkyl, hydrazonalkyl, lower alkylhydrazonoalkyl, phenylhydrazonoalkyl, cyano, carbamoyl having the same or different hydrogen atoms, lower alkyl, lower acyl, haloalkylcarbonyl, lower alkylsulfonyl, haloalkylsulfonyl or phenyl which is optionally substituted by alkyl, alkoxy or halogen, each of said carbamoyl substituents being on the nitrogen atom; phenyl which is optionally substituted by halogen, benzyl which is optionally substituted by alkyl, cyanoalkyl, carbamoylalkyl, thiocyanoalkyl, nitro, hydroxyamino, oxiranyl which is optionally substituted by alkyl; amino having the same or different hydrogen atoms, lower alkyl, haloalkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, alkylsulfonyl, haloalkylsulfonyl, phenylsulfonyl which is optionally substituted by alkyl, alkoxy or halogen, acyl, haloalkylcarbonyl or benzoyl which is optionally substituted, by alkyl, alkoxy or halogen, each of said amino substituents being on the nitrogen atom, or a group of the formula: ##STR94## wherein Z is an oxygen atom or a sulfur atom, W is a group of the formula --SO-- or a group of the formula --SO₂ --;R⁶ is hydrogen or lower alkyl; R⁷ is hydrogen, lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, haloalkyl, lower alkoxyalkyl or lower alkylthioalkyl; or R⁶ and R⁷ bond to each other to form a 3- to 8-membered (carbon) ring together with the carbon atom to which they are bonded; R⁸ is a hydrogen atom, lower alkyl, lower cycloalkyl, lower haloalkyl, lower alkoxycarbonylalkyl, hydroxycarbonylalkyl, monoalkylcarbamoylalalkyl, dialkylcarbamoylalkyl, lower acyl, lower alkylsulfonyl, haloalkylsulfonyl, haloalkylcarbonyl, monoalkylcarbamoyl, monoalkylthiocarbamoyl, dialkylcarbamoyl, dialkylthiocarbamoyl or benzoyl; R⁹ is a hydrogen atom, lower alkyl, lower cycloalkyl, lower haloalkyl, lower alkoxycarbonylalkyl, hydroxycarbonylalkyl, monoalkylcarbamoylalkyl or dialkylcarbamoylalkyl; R¹⁰ is a hydrogen atom, lower alkyl, lower acyl, alkylsulfonyl, haloalkylsulfonyl or haloalkylcarbonyl, R¹¹ is a hydrogen atom, lower alkyl, lower cycloalkyl, lower alkenyl, lower alkynyl, haloalkyl, lower alkoxyalkyl, alkylthioalkyl, phenyl which is optionally substituted by halogen, alkoxy, haloalkoxy, benzyloxy which is optionally substituted by halogen, phenoxy which is optionally substituted by alkoxy, or hydroxyl; and R⁴ is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, bromomethyl, dibromomethyl, tribromomethyl, difluoromethyl, hydroxymethyl, --CH(CH₃)OH, --CH₂ OCH₃, --CH₂ OC₂ H₅, --CH₂ OC₂ H₅, --CH₂ OCOCH₃, --CH₂ OCOC₂ H₅, --CH(CH₃)OCOCH₃, ##STR95## --CH₂ SCH₃, --CH₂ SO₂ CH₃, --CH₂ SC₂ H₅, --CH₂ SO₂ C₂ H₅, --CH₂ N(CH₃)₂, --CH₂ N(C₂ H₅)₂, Cl, Br, --COCH₃, --COC₂ H₅, --CH₂ N(C₂ H₅)₂, Cl, Br, --COCH₃, --COC₂ H₅, --COC₃ H₇, --COC₃ H₇ -i, ##STR96## --CHO, --C(CH₃)═NOH, --C(CH₃)═NOCH₃, --C(CH₃)═NOC₂ H₅, --C(CH₃)═NCH₃, --C(CH₃)═NNHCH₃, --CN, --COOH, --COOCH₃, --COOC₂ H₅, --COOC₃ H₇ -i, --COOC₅ --H₁₁, ##STR97## --CONH₂, --CONHCH₃, --CON(CH₃)₂, --CONHC₂ H₅, ##STR98## --NO₂, --NH₂, --NHCOCH₃, --NHCOCH₂ Cl, --NHCOCF₃, ##STR99## --NHSO₂ CH₃ --, --NHSO₂ CF₃, --NHSO₂ CH₂ Cl, --NHSO₂ CHF₂, ##STR100## --CH₂ N(C₂ H₅)₂, --CH(CH₃)Cl, --CH(CH₃),Br, --CH(CH₃)OCH₃, --CH(C₂ H₅)Cl, ##STR101## --COC₄ H₉ -n, --COCH₂ Cl, --COCH₂ Br, --COCH₂ Cl, --COCH₂ Br, --CH(OH)C₂ H₅, --CH(OH)C₃ H₇, --CH(OH)C₃ H₇ -i, --CH(OH)C.tbd.CH, --CH(OH)CH═CH₂, --CH₂ SC₃ H₇, --CH₂ SO₂ C₃ H₇, --CH₂ SC₃ H₇ -i, --CH₂ SO₂ C₃ H₇ -i, --CH₂ SC₄ H₉, --CH₂ SO₂ C₄ H₉, --CH═CH2, --C.tbd.CH, --CH₂ SO₂ CH₂ CF₃, ##STR102## CH═CHCH₃, C(CH₃)═CH₂, C(CH₃)═CHCH₃, C(C₂ H₅)═CH₂, C(C₂ H₅)═CHCH₃, C(CH₃)═C(CH₃)₂, CH═C(CH₃)₂, CH(CH₃)₅ CH₂ CF₃, CH(C₂ H₅)OCH₃, CH(CH₃)OCH₂ CH₂ F, CH(CH═CH₂)OCH₂ CF₃, and CH(CH₃)SCSN(C₂ H₅)₂.
 2. The benzofiran-7-yl uracil compound of claim 1, wherein X is fluorine or chlorine.
 3. The benzofuran-7-yl uracil compound of claim 1, wherein Y is fluorine, chlorine or bromine.
 4. The benzofuran-7-yl uracil compound of claim 1, wherein R¹ is methyl, amino, ethyl, propyl, chloromethyl or difluoromethyl.
 5. The benzofuran-7-yl uracil compound of claim 1, wherein R² is trifluoromethyl or chloromethyl.
 6. The benzofuran-7-yl uracil compound of claim 1, wherein R³ is hydrogen, methyl, chloromethyl or chloro.
 7. The benzofuran-7-yl uracil compound of claim 1, wherein R⁵ is hydrogen, lower alkyl, halogen, cyano, nitro, amino, carboxyl, or hydroxymethyl.
 8. A herbicide composition, comprising an amount of one or more benzofuran-7-yl uracil compounds of claim 1, and a carrier.
 9. A method of controlling weed growth, which comprises applying a herbicidally effective amount of one or more of the compounds of claim 1 to a soil area either before or during a growing stage in said soil area.
 10. The method of claim 9, wherein said weed growth controlled is annual or perennial weed growth.
 11. The method of claim 9, wherein said soil area is an upland field. 